| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-07-21 20:26:35 UTC |
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| Update Date | 2014-12-24 20:25:51 UTC |
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| Accession Number | T3D2749 |
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| Identification |
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| Common Name | Codeine |
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| Class | Small Molecule |
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| Description | In the United States, codeine is regulated by the Controlled Substances Act. It is a Schedule II controlled substance for pain-relief products containing codeine alone. In combination with aspirin or acetaminophen (paracetamol/tylenol) it is listed as Schedule III. Codeine is also available outside the United States as an over-the-counter drug (Schedule V) in liquid cough-relief formulations. Internationally, codeine is a Schedule II drug under the Single Convention on Narcotic Drugs. In the United Kingdom, codeine is regulated by the Misuse of Drugs Act 1971; it is a Class B Drug, except for concentrations of less than 8mg when combined with paracetamol - or 12.5mg when combined with ibuprofen - which are available in many over the counter preparations. it is a Class B Drug, except for concentrations of less than 8mg when combined with paracetamol - or 12.5mg when combined with ibuprofen - which are available in many over the counter preparations. An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. Codeine or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. It is marketed as the salts codeine sulfate and codeine phosphate. Codeine hydrochloride is more commonly marketed in contintental Europe and other regions. Codeine is an alkaloid found in opium in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. In the United Kingdom, codeine is regulated by the Misuse of Drugs Act 1971; Codeine or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. It is marketed as the salts codeine sulfate and codeine phosphate. Codeine hydrochloride is more commonly marketed in contintental Europe and other regions. Codeine is an alkaloid found in opium in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. Theoretically, a dose of approximately 200 mg (oral) of codeine must be administered to give equivalent analgesia to 30 mg (oral) of morphine (Rossi, 2004). It is not used, however, in single doses of greater than 60mg (and no more than 240 mg in 24 hours) since there is a ceiling effect. [PubChem]Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Codeine's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability. |
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| Compound Type | - Amine
- Analgesic
- Analgesic, Opioid
- Antitussive Agent
- Drug
- Ether
- Food Toxin
- Metabolite
- Narcotic
- Opiate Agonist
- Organic Compound
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | (-)-Codeine | | (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol | | (5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol | | 3-Methylmorphin | | 3-methylmorphine | | 7,8-Didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol | | Actacode | | Bisoltus | | Bromophar | | Bronchicum | | Bronchodine | | Codant | | Codedrill | | Codein | | Codeína | | Codeine anhydrous | | Codeinum | | Codeisan | | Coderpina | | Codicalm | | Codicept | | Codinex | | Coducept | | Cougel | | Coutan | | Dinco | | Farmacod | | Galcodine | | L-Codeine | | Methylmorphine | | Morphine 3-methyl ether | | Morphine monomethyl ether | | morphine-3-methyl ether | | Norcodeine, N-Methyl | | Norcodine, N-Methyl | | O(3)-Methylmorphine | | O3-Methylmorphine | | Pectoral | | Tussoret |
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| Chemical Formula | C18H21NO3 |
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| Average Molecular Mass | 299.364 g/mol |
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| Monoisotopic Mass | 299.152 g/mol |
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| CAS Registry Number | 76-57-3 |
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| IUPAC Name | (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol |
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| Traditional Name | (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol |
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| SMILES | [H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@]2([H])O |
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| InChI Identifier | InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1 |
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| InChI Key | InChIKey=OROGSEYTTFOCAN-DNJOTXNNSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Morphinans |
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| Sub Class | Not Available |
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| Direct Parent | Morphinans |
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| Alternative Parents | |
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| Substituents | - Morphinan
- Phenanthrene
- Tetralin
- Coumaran
- Anisole
- Aralkylamine
- Alkyl aryl ether
- Benzenoid
- Piperidine
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Ether
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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| Biofluid Locations | Not Available |
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| Tissue Locations | |
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| Pathways | | Name | SMPDB Link | KEGG Link |
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| Codeine Pathway | Not Available | Not Available |
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| Applications | |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 157.5°C | | Boiling Point | 250°C at 2.20E+01 mm Hg | | Solubility | 9000 mg/L (at 20°C) | | LogP | 1.19 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00lr-3090000000-38668348c3e45e16a9e7 | 2017-08-28 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0ab9-9135000000-5476697a08758d9606ba | 2017-10-06 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL Thermo Scientific) 60V, Positive | splash10-0uxr-0973000000-87d07ddd2ed24b9598d7 | 2015-11-06 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0009000000-d68b67071bf467a42afa | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0009000000-a298cedb776a11677cf7 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0459000000-1a92521b38ba51a7fa81 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0gc1-0940000000-68cae285315cfe9c7d0e | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0uxs-0910000000-b0c288c76c616e1a54d3 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0159-0390000000-ac30542a576060b3373c | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0009000000-870de7833257cd342810 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0009000000-8ece718ed46e5e439112 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0139000000-7880499a47dbd2f41229 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0uxr-0973000000-87d07ddd2ed24b9598d7 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-015a-0920000000-4f676c9e2b42320493af | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0uxr-0910000000-e67964930533268605cd | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0009000000-99b083bf48ae39e3cec6 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0009000000-efebfbff05a4cb72fe32 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0139000000-be0f9b6eaa028b54ad6c | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0uxr-0973000000-89bc81638a52beefd890 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-015a-0920000000-7eccc8e19d8d88b18128 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0uxr-0910000000-5809a9ed32210bcfa231 | 2017-09-14 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0029000000-426a3155887524f062f8 | 2017-07-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-1098000000-e16cf5105c8be7f2dd00 | 2017-07-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-4090000000-7d22a9e9b2e7b780b7b6 | 2017-07-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-d34a35c4caed20d97ad0 | 2017-07-26 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0090000000-16ee1c88e7d182e8ebf4 | 2017-07-26 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003f-1290000000-b1e3ca03a80d7ea7edab | 2017-07-26 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-01ot-3950000000-e80ecb11646b4da6aa92 | 2014-09-20 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral, Intramuscular.
Well absorbed following oral administration with a bioavailability of approximately 90%. Maximum plasma concentration occurs 60 minutes post-administration. Food does not effect the rate or extent of absorption of codeine. |
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| Mechanism of Toxicity | Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Codeine's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability. |
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| Metabolism | Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6 to morphine. 70-80% of the dose undergoes glucuronidation to form codeine-6-glucuronide. This process is mediated by UDP-glucuronosyltransferase UGT2B7 and UGT2B4. 5-10% of the dose undergoes O-demethylation to morphine and 10% undergoes N-demethylation to form norcodeine. CYP2D6 mediates the biotransformation to morphine. CYP3A4 is the enzymes that mediates the conversion to norcodiene. Morphine and norcodeine are further metabolized and undergo glucuronidation. The glucuronide metabolites of morphine are morphine-3-glucuronide (M3G) and morphine-6-glucuronide (M6G). Both morphine and morphine-6-glucuronide are active and have analgesic activity. Norcodiene and M3G do not have any analgesic properties.
Route of Elimination: 90% of the total dose of codeine is excreted through the kidneys, of which 10% is unchanged codeine.
Half Life: Plasma half-lives of codeine and its metabolites have been reported to be approximately 3 hours. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | For treatment and management of pain (systemic). It is also used as an antidiarrheal and as a cough suppressant. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose. |
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| Symptoms | Respiratory depression, sedation and miosis and common symptoms of overdose. Other symptoms include nausea, vomiting, skeletal muscle flaccidity, bradycardia, hypotension, and cool, clammy skin. Apnea and death may ensue. |
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| Treatment | Naloxone antagonizes most effects of codeine. Protect the airway as Naloxone may induce vomiting. Naloxone has a shorter duration of action than codeine; repeated doses may be needed. Protect the patient's airway and support ventilation and perfusion. Meticulously monitor and maintain, within acceptable limits, the patient's vital signs, blood gases, serum electrolytes, etc. Absorption of drugs from the gastrointestinal tract may be decreased by giving activated charcoal, which in many cases, is more effective than emesis or lavage; consider charcoal instead of or in addition to gastric emptying. Repeated doses of charcoal over time may hasten elimination of some drugs that have been absorbed. Safeguard the patient's airway when employing gastric emptying or charcoal. (25) |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB00318 |
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| HMDB ID | HMDB04995 |
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| PubChem Compound ID | 5284371 |
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| ChEMBL ID | CHEMBL485 |
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| ChemSpider ID | 4447447 |
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| KEGG ID | C06174 |
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| UniProt ID | Not Available |
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| OMIM ID | 124030 , 608902 |
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| ChEBI ID | 16714 |
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| BioCyc ID | CODEINE |
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| CTD ID | Not Available |
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| Stitch ID | Codeine |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Codeine |
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| References |
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| Synthesis Reference | Nagaraj R. Ayyangar, Anil R. Choudhary, Uttam R. Kalkote, Vasant K. Sharma, “Process for the preparation of codeine from morphine.” U.S. Patent US4764615, issued May, 1912. |
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| MSDS | Link |
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| General References | - Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. [15495019 ]
- Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [11092114 ]
- Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [15102399 ]
- Wilkins DG, Haughey HM, Krueger GG, Rollins DE: Disposition of codeine in female human hair after multiple-dose administration. J Anal Toxicol. 1995 Oct;19(6):492-8. [8926744 ]
- Ammon S, von Richter O, Hofmann U, Thon KP, Eichelbaum M, Mikus G: In vitro interaction of codeine and diclofenac. Drug Metab Dispos. 2000 Oct;28(10):1149-52. [10997932 ]
- Ropero-Miller JD, Lambing MK, Winecker RE: Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization. J Anal Toxicol. 2002 Oct;26(7):524-8. [12423011 ]
- Joseph RE Jr, Hold KM, Wilkins DG, Rollins DE, Cone EJ: Drug testing with alternative matrices II. Mechanisms of cocaine and codeine deposition in hair. J Anal Toxicol. 1999 Oct;23(6):396-408. [10517543 ]
- Paul BD, Shimomura ET, Smith ML: A practical approach to determine cutoff concentrations for opiate testing with simultaneous detection of codeine, morphine, and 6-acetylmorphine in urine. Clin Chem. 1999 Apr;45(4):510-9. [10102911 ]
- Skopp G, Potsch L, Moeller MR: On cosmetically treated hair--aspects and pitfalls of interpretation. Forensic Sci Int. 1997 Jan 17;84(1-3):43-52. [9042709 ]
- Piekoszewski W, Janowska E, Stanaszek R, Pach J, Winnik L, Karakiewicz B, Kozielec T: Determination of opiates in serum, saliva and hair addicted persons. Przegl Lek. 2001;58(4):287-9. [11450354 ]
- Hebden JM, Gilchrist PJ, Perkins AC, Wilson CG, Spiller RC: Stool water content and colonic drug absorption: contrasting effects of lactulose and codeine. Pharm Res. 1999 Aug;16(8):1254-9. [10468028 ]
- Huestis MA, Oyler JM, Cone EJ, Wstadik AT, Schoendorfer D, Joseph RE Jr: Sweat testing for cocaine, codeine and metabolites by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Oct 15;733(1-2):247-64. [10572984 ]
- Sindrup SH, Hofmann U, Asmussen J, Mikus G, Brosen K, Nielsen F, Ingwersen SH, Broen Christensen C: Impact of quinidine on plasma and cerebrospinal fluid concentrations of codeine and morphine after codeine intake. Eur J Clin Pharmacol. 1996;49(6):503-9. [8706777 ]
- Klein G, Barkworth MF, Birkenfeld A, Dyde CJ, Rehm KD, Toberich H, Cierpka H: [Relative bioavailability of paracetamol from tablets and suppositories as well as of paracetamol and codeine in a combination tablet]. Arzneimittelforschung. 1986 Mar;36(3):496-9. [3518729 ]
- O'Neal CL, Crouch DJ, Rollins DE, Fatah A, Cheever ML: Correlation of saliva codeine concentrations with plasma concentrations after oral codeine administration. J Anal Toxicol. 1999 Oct;23(6):452-9. [10517550 ]
- Hill V, Cairns T, Cheng CC, Schaffer M: Multiple aspects of hair analysis for opiates: methodology, clinical and workplace populations, codeine, and poppy seed ingestion. J Anal Toxicol. 2005 Oct;29(7):696-703. [16419403 ]
- Yue QY, Hasselstrom J, Svensson JO, Sawe J: Effect of codeine on oro-cecal transit time in Chinese healthy volunteers in comparison with Caucasian subjects. Eur J Clin Pharmacol. 1999 Jan;54(11):839-42. [10027657 ]
- Jonasson U, Jonasson B, Saldeen T, Thuen F: The prevalence of analgesics containing dextropropoxyphene or codeine in individuals suspected of driving under the influence of drugs. Forensic Sci Int. 2000 Aug 14;112(2-3):163-9. [10940601 ]
- Kintz P, Tracqui A, Mangin P: Analysis of opiates in fly larvae sampled on a putrefied cadaver. J Forensic Sci Soc. 1994 Apr-Jun;34(2):95-7. [8035160 ]
- Hofmann U, Seefried S, Schweizer E, Ebner T, Mikus G, Eichelbaum M: Highly sensitive gas chromatographic-tandem mass spectrometric method for the determination of morphine and codeine in serum and urine in the femtomolar range. J Chromatogr B Biomed Sci Appl. 1999 Apr 30;727(1-2):81-8. [10360425 ]
- Hepler BR, Sutheimer C, Sunshine I, Sebrosky GF: Combined enzyme immunoassay-LCEC method for the identification, confirmation, and quantitation of opiates in biological fluids. J Anal Toxicol. 1984 Mar-Apr;8(2):78-90. [6371380 ]
- Joseph RE Jr, Oyler JM, Wstadik AT, Ohuoha C, Cone EJ: Drug testing with alternative matrices I. Pharmacological effects and disposition of cocaine and codeine in plasma, sebum, and stratum corneum. J Anal Toxicol. 1998 Jan-Feb;22(1):6-17. [9491963 ]
- Pascual JA, Sanagustin J: Fully automated analytical method for codeine quantification in human plasma using on-line solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 1999 Mar 19;724(2):295-302. [10219671 ]
- Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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