| Version |
1.0 |
| Creation Date |
2009-07-21 20:27:02 |
| Update Date |
2010-05-18 21:00:06 |
| Accession Number |
T3D2810 |
| Name |
Cimetidine |
| Compound Type |
- Adjuvant
- Analgesic
- Anti-Ulcer Agent
- Drug
- Enzyme Inhibitor
- Histamine Antagonist
- Histamine H2 Antagonist
|
| Description |
Cimetidine is a histamine congener, it competitively inhibits histamine binding to histamine H2 receptors. Cimetidine has a range of pharmacological actions. It inhibits gastric acid secretion, as well as pepsin and gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy. [PubChem] |
| Synonyms |
- Cimetidine A/AB
- Cimetidine Hcl
|
| Chemical IUPAC Name |
1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine |
| Chemical Formula |
C10H16N6S |
| Chemical Structure |
 |
| CAS Registry Number |
51481-61-9 |
| InChI Identifier |
InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14) |
| InChI Key |
InChIKey=AQIXAKUUQRKLND-UHFFFAOYSA-N |
| PubChem Compound ID |
2756  |
| KEGG ID |
Not Available |
| UniProt ID |
Not Available |
| OMIM ID |
Not Available |
| ChEBI ID |
30731 |
| BioCyc ID |
Not Available |
| SuperToxic ID |
Not Available |
| CTD ID |
Not Available |
| Stitch ID |
Cimetidine |
| DrugBank ID |
DB00501 |
| PDB ID |
Not Available |
| ACToR ID |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Cimetidine |
| Monoisotopic Mass |
252.115715 |
| MOL File |
Show |
| PDB File |
Show |
| SDF File |
Show |
| SMILES |
CN=C(NCCSCC1=C(C)NC=N1)NC#N |
| Appearance |
Not Available |
| Melting Point |
142 oC |
| Solubility |
0.5 g/100 mL |
| Predicted LogP |
-0.1094 |
| Route of Exposure |
Oral |
| Mechanism of Action |
Cimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity. |
| Metabolism |
Hepatic |
| Toxicity Values |
Not Available |
| Lethal Dose |
Not Available |
| Carcinogenicity (IARC Classification) |
Not Available |
| Uses/Sources |
Largely used in the treatment of heartburn and peptic ulcers. [Wikipedia] |
| Minimum Risk Level |
Not Available |
| Health Effects |
Not Available |
| Symptoms |
Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat. |
| Treatment |
The usual measures to remove unabsorbed material from the gastrointestinal tract, clinical monitoring and supportive therapy should be employed. (V650) |
| General References |
- T874 - Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4. [PubMed ]
- T873 - Drugs.com
- V650 - RxList: The Internet Drug Index (2009).
|
| Targets |
- Histamine H2 receptor
- Putative renal organic anion transporter 1
|
|
Target 1
[top]
|
| Target 1 ID |
1178 |
| Target 1 Name |
Histamine H2 receptor |
| Target 1 Mechanism of Action |
Cimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity. |
| Target 1 Description |
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway (By similarity) |
| Target 1 Synonyms |
- H2R; Gastric receptor I
|
| Target 1 Gene Name |
HRH2 |
| Target 1 Protein Sequence |
>Histamine H2 receptor
MAPNGTASSFCLDSTACKITITVVLAVLILITVAGNVVVCLAVGLNRRLRNLTNCFIVSL
AITDLLLGLLVLPFSAIYQLSCKWSFGKVFCNIYTSLDVMLCTASILNLFMISLDRYCAV
MDPLRYPVLVTPVRVAISLVLIWVISITLSFLSIHLGWNSRNETSKGNHTTSKCKVQVNE
VYGLVDGLVTFYLPLLIMCITYYRIFKVARDQAKRINHISSWKAATIREHKATVTLAAVM
GAFIICWFPYFTAFVYRGLRGDDAINEVLEAIVLWLGYANSALNPILYAALNRDFRTGYQ
QLFCCRLANRNSHKTSLRSNASQLSRTQSREPRQQEEKPLKLQVWSGTEVTAPQGATDR
|
| Target 1 Number of Residues |
359 |
| Target 1 Molecular Weight |
40097.7 |
| Target 1 Theoretical pI |
9.39 |
| Target 1 GO Classification |
|
Function
|
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity |
|
Process
|
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway |
|
Component
|
cell
membrane
intrinsic to membrane
integral to membrane |
|
| Target 1 General Function |
Involved in histamine receptor activity |
| Target 1 Pathways |
Not Available |
| Target 1 Reactions |
Not Available |
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 23-44
- 58-81
- 93-114
- 135-159
- 181-204
- 235-258
- 268-289
|
| Target 1 Essentiality |
Non Essential |
| Target 1 Domain Function |
PF00001:7tm_1 |
| Target 1 GenBank ID Protein |
Not Available |
| Target 1 UniProtKB ID |
P25021 |
| Target 1 Cellular Location |
Cell membrane |
| Target 1 Gene Sequence |
Not Available |
| Target 1 GenBank Gene ID |
Not Available |
| Target 1 GeneCard ID |
HRH2 |
| Target 1 GenAtlas ID |
HRH2 |
| Target 1 HGNC ID |
HGNC:5183 |
| Target 1 Chromosome Location |
Not Available |
| Target 1 Locus |
5q35.2 |
| Target 1 SNPs |
SNPJam Report |
| Target 1 Toxin References |
- S918 - Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed ]
- T882 - Kuint J, Linder N, Reichman B: Hypoxemia associated with cimetidine therapy in a newborn infant. Am J Perinatol. 1996 Jul;13(5):301-3. [PubMed ]
- T881 - Takahashi HK, Watanabe T, Yokoyama A, Iwagaki H, Yoshino T, Tanaka N, Nishibori M: Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. Mol Pharmacol. 2006 Aug;70(2):450-3. Epub 2006 May 24. [PubMed ]
- T880 - Hernandez-Munoz R, Montiel-Ruiz C, Vazquez-Martinez O: Gastric mucosal cell proliferation in ethanol-induced chronic mucosal injury is related to oxidative stress and lipid peroxidation in rats. Lab Invest. 2000 Aug;80(8):1161-9. [PubMed ]
|
| Target 1 General References |
1714721; 7755641; 10371214; 15014171; 8817552; 9374694 |
|
Target 2
[top]
|
| Target 2 ID |
1209 |
| Target 2 Name |
Putative renal organic anion transporter 1 |
| Target 2 Mechanism of Action |
Cimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity. |
| Target 2 Description |
Not Available |
| Target 2 Synonyms |
Not Available |
| Target 2 Gene Name |
Not Available |
| Target 2 Protein Sequence |
Not Available |
| Target 2 Number of Residues |
Not Available |
| Target 2 Molecular Weight |
Not Available |
| Target 2 Theoretical pI |
Not Available |
| Target 2 GO Classification |
Not Available |
| Target 2 General Function |
Not Available |
| Target 2 Pathways |
Not Available |
| Target 2 Reactions |
Not Available |
| Target 2 Signals |
Not Available |
| Target 2 Transmembrane Regions |
Not Available |
| Target 2 Essentiality |
Not Available |
| Target 2 Domain Function |
Not Available |
| Target 2 GenBank ID Protein |
Not Available |
| Target 2 UniProtKB ID |
O95742 |
| Target 2 Cellular Location |
Not Available |
| Target 2 Gene Sequence |
Not Available |
| Target 2 GenBank Gene ID |
Not Available |
| Target 2 GeneCard ID |
Not Available |
| Target 2 GenAtlas ID |
Not Available |
| Target 2 HGNC ID |
Not Available |
| Target 2 Chromosome Location |
Not Available |
| Target 2 Locus |
Not Available |
| Target 2 SNPs |
Not Available |
| Target 2 Toxin References |
- T879 - Ueo H, Motohashi H, Katsura T, Inui K: Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13. [PubMed ]
- T878 - Motohashi H, Uwai Y, Hiramoto K, Okuda M, Inui K: Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). Eur J Pharmacol. 2004 Oct 25;503(1-3):25-30. [PubMed ]
- T876 - Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [PubMed ]
- T877 - Hashimoto T, Narikawa S, Huang XL, Minematsu T, Usui T, Kamimura H, Endou H: Characterization of the renal tubular transport of zonampanel, a novel alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptor antagonist, by human organic anion transporters. Drug Metab Dispos. 2004 Oct;32(10):1096-102. [PubMed ]
- T875 - Burckhardt BC, Brai S, Wallis S, Krick W, Wolff NA, Burckhardt G: Transport of cimetidine by flounder and human renal organic anion transporter 1. Am J Physiol Renal Physiol. 2003 Mar;284(3):F503-9. Epub 2002 Nov 12. [PubMed ]
|
| Target 2 General References |
Not Available |
