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51481-61-9

Basic Information
CAS No.: 51481-61-9
Name: Cimetidine
Molecular Structure:
Molecular Structure of 51481-61-9 (Cimetidine)
Formula: C10H16N6S
Molecular Weight: 252.38
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;
EINECS: 257-232-2
Density: 1.27 g/cm3
Melting Point: 139-144 °C
Boiling Point: 488 °C at 760 mmHg
Flash Point: 248.9 °C
Solubility: 0.5 g/100 mL at 20 °C in water
Appearance: white solid
Hazard Symbols: ToxicT,HarmfulXn
Risk Codes: 60-42/43-36/37/38-20/22
Safety: 53-26-36/37/39-45-36-22
Transport Information:
PSA: 114.19000
LogP: 1.37918
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Chemistry


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

History

 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.

Uses

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. 

Production

 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

Toxicity Data With Reference

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.

Safety Profile

Hazard Codes: ToxicT,HarmfulXn
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

Specification

  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.

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