Cimetidine

Modify Date: 2024-01-02 16:16:04

Cimetidine Structure
Cimetidine structure
 Common Name Cimetidine
CAS Number 51481-61-9 Molecular Weight 252.339
Density 1.3±0.1 g/cm3 Boiling Point 476.2±55.0 °C at 760 mmHg
Molecular Formula C10H16N6S Melting Point 139-144°C
MSDS Chinese USA Flash Point 241.8±31.5 °C
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Cimetidine


Cimetidine is a histamine-2 (H2) receptor antagonist.IC50 Value: Target: Histamine-2 Receptorin vitro: Cimetidine, a partial agonist for H2R, has a pharmacological profile different from ranitidine and famotidine, possibly contributing to its antitumor activity on gastrointestinal cancers [1]. Cimetidine had no effect on the uptake and cytotoxicity of cisplatin in ovarian cancer cells with high OCT2 mRNA levels (IGROV-1 cells) [2]. Cimetidine showed no effect on proliferation, survival, migration and invasion of 3LL cells. Cimetidine reversed MDSC-mediated T-cell suppression, and improved IFN-γ production. [3]. Cimetidine-mediated down-regulation of NCAM involved suppression of the nuclear translocation of NF-kappaB, a transcriptional activator of NCAM gene expression [4].in vivo: the antitumor efficacy of cisplatin in mice bearing luciferase-tagged IGROV-1 xenografts was unaffected by cimetidine (P = 0.39). Data obtained in 18 patients receiving cisplatin (100 mg/m(2)) in a randomized crossover fashion with or without cimetidine (800 mg × 2) revealed that cimetidine did not alter exposure to unbound cisplatin [2]. cimetidine reduced CD11b(+)Gr-1(+) myeloid derived-suppressive cell (MDSC) accumulation in spleen, blood and tumor tissue of tumor-bearing mice [3]. Cimetidine exerts a beneficial effect on periodontal disease in rats, decreasing the RANKL/OPG ratio in gingival connective tissue and reducing alveolar bone resorption [5].

 Names

Name cimetidine
Synonym More Synonyms

 Cimetidine Biological Activity

Description Cimetidine is a histamine-2 (H2) receptor antagonist.IC50 Value: Target: Histamine-2 Receptorin vitro: Cimetidine, a partial agonist for H2R, has a pharmacological profile different from ranitidine and famotidine, possibly contributing to its antitumor activity on gastrointestinal cancers [1]. Cimetidine had no effect on the uptake and cytotoxicity of cisplatin in ovarian cancer cells with high OCT2 mRNA levels (IGROV-1 cells) [2]. Cimetidine showed no effect on proliferation, survival, migration and invasion of 3LL cells. Cimetidine reversed MDSC-mediated T-cell suppression, and improved IFN-γ production. [3]. Cimetidine-mediated down-regulation of NCAM involved suppression of the nuclear translocation of NF-kappaB, a transcriptional activator of NCAM gene expression [4].in vivo: the antitumor efficacy of cisplatin in mice bearing luciferase-tagged IGROV-1 xenografts was unaffected by cimetidine (P = 0.39). Data obtained in 18 patients receiving cisplatin (100 mg/m(2)) in a randomized crossover fashion with or without cimetidine (800 mg × 2) revealed that cimetidine did not alter exposure to unbound cisplatin [2]. cimetidine reduced CD11b(+)Gr-1(+) myeloid derived-suppressive cell (MDSC) accumulation in spleen, blood and tumor tissue of tumor-bearing mice [3]. Cimetidine exerts a beneficial effect on periodontal disease in rats, decreasing the RANKL/OPG ratio in gingival connective tissue and reducing alveolar bone resorption [5].
Related Catalog
References

[1]. Takahashi, H.K., et al., Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. Mol Pharmacol, 2006. 70(2): p. 450-3.

[2]. Sprowl, J.A., et al., Conjunctive therapy of cisplatin with the OCT2 inhibitor cimetidine: influence on antitumor efficacy and systemic clearance. Clin Pharmacol Ther, 2013. 94(5): p. 585-92.

[3]. Zheng, Y., et al., Cimetidine suppresses lung tumor growth in mice through proapoptosis of myeloid-derived suppressor cells. Mol Immunol, 2013. 54(1): p. 74-83.

[4]. Fukuda, M., K. Kusama, and H. Sakashita, Cimetidine inhibits salivary gland tumor cell adhesion to neural cells and induces apoptosis by blocking NCAM expression. BMC Cancer, 2008. 8: p. 376.

[5]. Longhini, R., et al., Cimetidine Reduces the Alveolar Bone Loss in Induced Periodontitis in Rat Molars. J Periodontol, 2013.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 476.2±55.0 °C at 760 mmHg
Melting Point 139-144°C
Molecular Formula C10H16N6S
Molecular Weight 252.339
Flash Point 241.8±31.5 °C
Exact Mass 252.115707
PSA 114.19000
LogP 0.07
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.632
Storage condition 2-8°C
Water Solubility 0.5 g/100 mL at 20 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MF0035500
CHEMICAL NAME :
Guanidine, N-cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl )methyl)thio)ethyl)-
CAS REGISTRY NUMBER :
51481-61-9
LAST UPDATED :
199606
DATA ITEMS CITED :
50
MOLECULAR FORMULA :
C10-H16-N6-S
MOLECULAR WEIGHT :
252.38

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
51 mg/kg/3D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
30 mg/kg/2D-I
TOXIC EFFECTS :
Behavioral - ataxia Behavioral - rigidity (including catalepsy) Behavioral - muscle contraction or spasticity
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2857 ug/kg
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
57 mg/kg/5D-I
TOXIC EFFECTS :
Liver - jaundice, cholestatic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
80 mg/kg/8D
TOXIC EFFECTS :
Vascular - BP lowering not characterized in autonomic section Blood - leukopenia Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
270 mg/kg/3W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - interstitial nephritis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
4286 ug/kg/30M-C
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea Skin and Appendages - sweating
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1008 mg/kg/6W-I
TOXIC EFFECTS :
Vascular - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
4 mg/kg/2M-C
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
600 mg/kg/6W
TOXIC EFFECTS :
Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
328 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
860 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
106 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2550 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
306 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
437 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
206 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Gastrointestinal - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>8640 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1063 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
164 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
880 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 gm/kg/30D-C
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
364 gm/kg/26W-C
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
123 gm/kg/13W-I
TOXIC EFFECTS :
Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in prostate weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1400 mg/kg/14D-I
TOXIC EFFECTS :
Immunological Including Allergic - increase in cellular immune response Immunological Including Allergic - increase in humoral immune response Immunological Including Allergic - increased immune response
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
7392 mg/kg/11D-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
15600 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - testicular tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
13300 mg/kg male 2 week(s) pre-mating female 2 week(s) pre-mating - 3 week(s) post-birth
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
39312 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - testicular tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
720 mg/kg
SEX/DURATION :
female 33-37 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - hepatobiliary system Reproductive - Effects on Newborn - Apgar score (human only)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 mg/kg
SEX/DURATION :
male 7 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4384 mg/kg
SEX/DURATION :
female 12-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - delayed effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4950 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1650 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
14850 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2100 mg/kg
SEX/DURATION :
lactating female 42 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
1820 mg/kg
SEX/DURATION :
male 26 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

MUTATION DATA

TYPE OF TEST :
Unscheduled DNA synthesis
TEST SYSTEM :
Rodent - rat Liver
DOSE/DURATION :
1 mmol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 120,133,1983 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,235,1990 IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,235,1990 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,235,1990 TOXICOLOGY REVIEW SUMEA4 Suvremenna Meditsina. Modern Medicine. (Hemus, Blvd. Russki 6, Sofia, Bulgaria) V.1- 1951- Volume(issue)/page/year: 32,472,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3652 No. of Facilities: 248 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 11103 (estimated) No. of Female Employees: 9115 (estimated)

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H360
Precautionary Statements P201-P308 + P313
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T:Toxic;
Risk Phrases R60
Safety Phrases S53-S26-S36/37/39-S45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS MF0035500
HS Code 2933990090

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

1-Cyano-2-methyl-3-(2-{[(4-methyl-1H-imidazol-5-yl)methyl]sulfanyl}ethyl)guanidine
Acinil
EINECS 257-232-2
Cimetidine
Guanidine, N-cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)-
ULCIMET
2-Cyano-1-methyl-3-[2-(5-methyl-1H-imidazol-4-yl-methylthio)ethyl]guanidine
1-Cyano-3-methyl-2-(2-{[(4-methyl-1H-imidazol-5-yl)methyl]sulfanyl}ethyl)guanidine
Cimal
Guanidine, N-cyano-N''-methyl-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-
N-Cyano-N'-methyl-N''-[2-[[(4-methyl-1H-imidazol-5-yl)methyl]thio]ethyl]guanidine
guanidine, N-cyano-N'-methyl-N''-[2-[[(4-methyl-1H-imidazol-5-yl)methyl]thio]ethyl]-
Dyspamet
Brumetadina
MFCD00133296
Tagamet
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