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Name |
Cimetidine |
EINECS | 257-232-2 |
CAS No. | 51481-61-9 | Density | 1.27 g/cm3 |
PSA | 114.19000 | LogP | 1.37918 |
Solubility | 0.5 g/100 mL at 20 °C in water | Melting Point |
139-144 °C |
Formula | C10H16N6S | Boiling Point | 488 °C at 760 mmHg |
Molecular Weight | 252.343 | Flash Point | 248.9 °C |
Transport Information | N/A | Appearance | white solid |
Safety | 53-26-36/37/39-45-36-22 | Risk Codes | 60-42/43-36/37/38-20/22 |
Molecular Structure | Hazard Symbols | T,Xn | |
Synonyms |
Cimetidine Type A/ AB;Clotrimazole;CB4229414;cimetidine A/AB;FPF 1002;Cimetidin AB;Cimetidine Form AB;Cimetidine Type AB/Type A;CIMETIDINE USP24;Guanidine, N-cyano-N-methyl-N-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio) ethyl)-;Guanidine, N-cyano-N-methyl-N-[2-[[ (5-methyl-1H-imidazol-4-yl)methyl]thio] ethyl]-;Acinil;Ulcimet;1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine;Metracin;Histodil;Prestwick_65; |
Article Data | 45 |
IUPAC Name: 1-Cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
Molecular Formula: C10H16N6S
Molecular Weight: 252.34 g/mol
EINECS: 257-232-2
Classification Code: Antagonist [to histamine H2 receptors]; Anti-ulcer agents; Drug / Therapeutic Agent; Enzyme inhibitors; Gastrointestinal Agents; Histamine Agents; Histamine Antagonists; Histamine H2 antagonists; Human Data; Mutation data; Neurotransmitter Agents; Reproductive Effect; Tumor data
Melting Point: 139-144 °C
storage temp.: 2-8 °C
Water Solubility: 0.5 g/100 mL at 20 °C
Index of Refraction: 1.631
Molar Refractivity: 70.7 cm3
Molar Volume: 198.2 cm3
Surface Tension: 49.5 dyne/cm
Density: 1.27 g/cm3
Flash Point: 248.9 °C
Enthalpy of Vaporization: 75.4 kJ/mol
Boiling Point: 488 °C at 760 mmHg
Vapour Pressure of Cimetidine (CAS NO.51481-61-9): 1.13E-09 mmHg at 25 °C
Cimetidine (CAS NO.51481-61-9) was the prototypical histamine H2-receptor antagonist from which the later members of the class were developed. Cimetidine (CAS NO.51481-61-9) was the culmination of a project at Smith, Kline & French by James W. Black, C. Robin Ganellin, and others to develop a histamine receptor antagonist to suppress stomach acid secretion.
At the time (1964) it was known that histamine was able to stimulate the secretion of stomach acid, but also that traditional antihistamines had no effect on acid production. In the process, the SK&F scientists also proved the existence of histamine H2-receptors.
Cimetidine (CAS NO.51481-61-9) was first marketed in the United Kingdom in 1976; therefore, it took 12 years from initiation of the H2-receptor antagonist program to commercialization. Subsequent to the introduction onto the U.S. drug market, two other H2-receptor antagonists were approved, ranitidine and famotidine Cimetidine became the first drug ever to reach more than $1 billion a year in sales, thus making it the first blockbuster drug.
Cimetidine (CAS NO.51481-61-9) is widely used as an antiulcer medication. It is used to inhibits gastric acid secretion and reduces Pepsin output; and used in treatment of colorectal cancer. It is also uesd as an analgesic in experimental treatments of interstitial cystitis.
Cimetidine (CAS NO.51481-61-9) is manufactured by the action of a substituted guanidine on an amino-thio compound in the presence of methyl cyanide.
CH3NHCSCH3 + NH2CH2CH2SCH2Z → CH3NHCNHCH2CH2SCH2Z
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | intravenous | 100mg/kg (100mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP | Annals of Internal Medicine. Vol. 97, Pg. 283, 1982. |
dog | LD50 | intravenous | 206mg/kg (206mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE GASTROINTESTINAL: OTHER CHANGES | Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 2806, 1980. |
dog | LD50 | oral | 2600mg/kg (2600mg/kg) | Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 329, 1977. | |
hamster | LD50 | intraperitoneal | 880mg/kg (880mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Gastroenterology. Vol. 74, Pg. 339, 1978. |
hamster | LD50 | oral | 4gm/kg (4000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Gastroenterology. Vol. 74, Pg. 339, 1978. |
human | TDLo | oral | 80mg/kg/8D (80mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION BLOOD: LEUKOPENIA | Lancet. Vol. 1, Pg. 444, 1978. |
man | TDLo | intravenous | 4286ug/kg/30M (4.286mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Annals of Internal Medicine. Vol. 97, Pg. 374, 1982. |
man | TDLo | oral | 2857ug/kg (2.857mg/kg) | CARDIAC: OTHER CHANGES | Lancet. Vol. 1, Pg. 225, 1987. |
man | TDLo | oral | 51mg/kg/3D-I (51mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Medicine. Vol. 75, Pg. 875, 1983. |
man | TDLo | oral | 57mg/kg/5D-I (57mg/kg) | LIVER: "JAUNDICE, CHOLESTATIC" | Digestive Diseases and Sciences. Vol. 32, Pg. 333, 1987. |
man | TDLo | oral | 270mg/kg/3W-I (270mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS | American Journal of Medicine. Vol. 70, Pg. 1272, 1981. |
man | TDLo | unreported | 600mg/kg/6W (600mg/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Lancet. Vol. 1, Pg. 1160, 1981. |
mouse | LD50 | intraperitoneal | 306mg/kg (306mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 1655, 1983. | |
mouse | LD50 | intravenous | 150mg/kg (150mg/kg) | Journal of International Medical Research. Vol. 3, Pg. 86, 1975. | |
mouse | LD50 | oral | 2550mg/kg (2550mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. | |
mouse | LD50 | subcutaneous | 437mg/kg (437mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. | |
rabbit | LD50 | intraperitoneal | 1063mg/kg (1063mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. | |
rabbit | LD50 | intravenous | 164mg/kg (164mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. | |
rabbit | LD50 | oral | > 8640mg/kg (8640mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. |
rat | LD50 | intraperitoneal | 328mg/kg (328mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. | |
rat | LD50 | intravenous | 106mg/kg (106mg/kg) | Journal of International Medical Research. Vol. 3, Pg. 86, 1975. | |
rat | LD50 | oral | 5gm/kg (5000mg/kg) | Journal of International Medical Research. Vol. 3, Pg. 86, 1975. | |
rat | LD50 | subcutaneous | 860mg/kg (860mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983. | |
women | LDLo | intravenous | 1008mg/kg/6W- (1008mg/kg) | VASCULAR: OTHER CHANGES | Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 126, 1983. |
women | TDLo | intravenous | 4mg/kg/2M-C (4mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP | Lancet. Vol. 1, Pg. 99, 1987. |
women | TDLo | oral | 30mg/kg/2D-I (30mg/kg) | BEHAVIORAL: ATAXIA BEHAVIORAL: REGIDITY BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Annals of Emergency Medicine. Vol. 16, Pg. 1162, 1987. |
Hazard Codes: T,Xn
Risk Statements: 60-42/43-36/37/38-20/22
R60:May impair fertility.
R42/43:May cause sensitization by inhalation and skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/22:Harmful by inhalation and if swallowed.
Safety Statements: 53-26-36/37/39-45-36-22
S53:Avoid exposure - obtain special instructions before use.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36:Wear suitable protective clothing.
S22:Do not breathe dust.
WGK Germany: 3
RTECS of Cimetidine (CAS NO.51481-61-9): MF0035500
Cimetidine (CAS NO.51481-61-9), its Synonyms are 1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine ; 2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine ; Acibilin ; Acinil ; Cimetag ; Cimetidina . It is white solid.