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692-13-7

692-13-7 structure
692-13-7 structure
  • Name: Buformin
  • Chemical Name: 1-butylbiguanide
  • CAS Number: 692-13-7
  • Molecular Formula: C6H15N5
  • Molecular Weight: 157.21700
  • Catalog: API Hormone and endocrine-regulating drugs Pancreatic hormones and other blood sugar regulating drugs
  • Create Date: 2018-06-03 08:00:00
  • Modify Date: 2024-01-04 22:53:13
  • Buformin (1-Butylbiguanide) is a potent and orally active biguanide antidiabetic agent, an AMPK activator. Buformin decreases hepatic gluconeogenesis and lowers blood glucose production in vivo. Buformin also has anti-cancer activities and is applied in cancer study (such as, cervical cancer and breast cancer, et al)[1].

Name 1-butylbiguanide
Synonyms Glybigid
Buformine
W 37
Dibetos B
Butformin
1-butyl-biguanide
Butylbiguanide
N-butylbiguanide
1-Butyl-biguanid
DBV
H 224
Buformin
Butyldiguanide
EINECS 211-726-4
Description Buformin (1-Butylbiguanide) is a potent and orally active biguanide antidiabetic agent, an AMPK activator. Buformin decreases hepatic gluconeogenesis and lowers blood glucose production in vivo. Buformin also has anti-cancer activities and is applied in cancer study (such as, cervical cancer and breast cancer, et al)[1].
Related Catalog
In Vitro Buformin (0-10 mM; 5 days) inhibits SKBR3 and BT474 cells growth as a concentration-dependent manner, exhibits IC50 values of 246.7 μM and  98.6 μM for erbB-2-overexpressing SKBR3 and BT474 cells, respectively[1]. Buformin (0-3 mM; 48 hours)  increases the percentage of cells in G0/G1 phase and reduced the percentage of cells in S phase, especially in the SKBR3 cells[1]. Buformin (0-3 mM; 24 hours) suppresses RTK activation, including erbB-2 and IGF1R signaling  downstream, and Akt activation/phosphorylation is inhibited in both SKBR3 and BT474 cells[1]. Cell Viability Assay[1] Cell Line: ErbB-2-overexpressing SKBR3 and BT474 cells Concentration: 0 μM, 1 μM, 3 μM, 10 μM, 30 μM, 100 μM, 300 μM, 1, 3, or 10 mM Incubation Time: 5 days Result: Reduced cell viability in erbB-2-overexpressing breast cells. Cell Cycle Analysis[1] Cell Line: ErbB-2-overexpressing SKBR3 and BT474 cells Concentration: 0.5 mM; 1 mM; 3 mM Incubation Time: 48 hours Result: Increased cells arresting in G0/G1 phase. Western Blot Analysis[1] Cell Line: ErbB-2-overexpressing SKBR3 and BT474 cells Concentration: 0 mM, 0.1 mM, 0.3 mM, 1 mM, or 3 mM Incubation Time: 24 hours Result: Decreased p-AMPK, p-p706S, p-ERK1/2 expression in a concentration-dependent manner.
In Vivo Buformin (oral administation; 7.6 mmol/kg of chow; 7 days) exhibits significantly reduced tumor volumes and weights, and hinders mammary morphogenesis and proliferation in MMTV-erbB-2 transgenic mice[1] Animal Model: Female MMTV-erbB-2 transgenic mice[1] Dosage: 7.6 mmol/kg Administration: Oral administation; 7 days Result: Inhibited mammary syngeneic tumor growth in MMTV-erbB-2 transgenic mice.
References

[1]. Amanda B Parris, et al. Buformin Inhibits the Stemness of erbB-2-overexpressing Breast Cancer Cells and Premalignant Mammary Tissues of MMTV-erbB-2 Transgenic Mice. J Exp Clin Cancer Res

[2]. Jing Li, et al. Buformin Suppresses Proliferation and Invasion via AMPK/S6 Pathway in Cervical Cancer and Synergizes With Paclitaxel. Cancer Biol Ther. 2018 Jun 3;19(6):507-517.

Density 1.22g/cm3
Boiling Point 322.7ºC at 760 mmHg
Molecular Formula C6H15N5
Molecular Weight 157.21700
Flash Point 148.9ºC
Exact Mass 157.13300
PSA 97.78000
LogP 1.47550
Index of Refraction 1.568

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DU1132000
CHEMICAL NAME :
Biguanide, 1-butyl-
CAS REGISTRY NUMBER :
692-13-7
BEILSTEIN REFERENCE NO. :
0607037
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C6-H15-N5
MOLECULAR WEIGHT :
157.26
WISWESSER LINE NOTATION :
MUYZMYUM&M4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,1521,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
140 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,1521,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MEXPAG Medicina Experimentalis. (Basel, Switzerland) V.1-11, 1959-64; V.18-19, 1968-69. For publisher information, see JNMDBO. Volume(issue)/page/year: 8,237,1963

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692-13-7 structure

692-13-7

Literature: Dutta,R.L.; Sengupta,N.R. Journal of the Indian Chemical Society, 1961 , vol. 38, p. 741 - 746

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692-13-7 structure

692-13-7

Literature: Shaw; Gross Journal of Organic Chemistry, 1959 , vol. 24, p. 1809 Full Text View citing articles Show Details Shapiro et al. Journal of the American Chemical Society, 1959 , vol. 81, p. 3725,3726

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692-13-7 structure

692-13-7

Literature: Urbanski et al. Roczniki Chemii, 1959 , vol. 33, p. 1383,1387 Chem.Abstr., 1960 , p. 13034
Precursor  2

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