CID 657277
Basic information
- CAS
834-28-6- Standard SMILES
NC(N)=NC(N)=NCCc1ccccc1.[Cl-].[H+]- InChIKey
YSUCWSWKRIOILX-UHFFFAOYSA-N- Molecular formula
- C10H16ClN5
- Average molar mass
- 241.72 g/mol
- Monoisotopic mass
- 241.1094232
Overview
See also: Phenformin Hydrochloride (preferred); Phenformin (has active moiety).
Names & identifiers
- Preferred name
- CID 657277
- IUPAC
- 1-(diaminomethylidene)-2-(2-phenylethyl)guanidine;hydron;chloride
- English name
- Phenformin hydrochloride
- Molecular formula
- C10H16ClN5
- Molecular weight
- 241.72
Names & synonyms
SCHEMBL787929AKOS0267501101-Phendbi-tdInsorameltrolusafvi-6GlucopostinPHENFORMIN HCLPhenformine HCLPhenforMin HCl APIphenforminhclno.9113
Database identifiers
- CAS
834-28-6- PubChem CID
- 657277
Properties
Computed structural properties
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 236
Physicochemical properties
- Melting point
- 175 · 175-178°C
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 10 g/100 · >=10 g/100 mL at 21 ºC
- InChI
- InChI=1S/C10H15N5.ClH/c11-9(12)15-10(13)14-7-6-8-4-2-1-3-5-8;/h1-5H,6-7H2,(H6,11,12,13,14,15);1H
- InChIKey
- YSUCWSWKRIOILX-UHFFFAOYSA-N
- SMILES
- N=C(NCCC1C=CC=CC=1)NC(=N)N.[H]Cl
- CAS DataBase Reference
- 834 · 834-28-6(CAS DataBase Reference)
- FDA UNII
- 91 XC93EU03 · 91XC93EU03
- NCI Drug Dictionary
- phenformin hydrochloride
- EPA Substance Registry System
- Phenformin hydrochloride (834-28-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- DU2200000
- hs_code
- 29252900
- Toxicity
- LD50 in mice (mg/kg): 19 i.v., 450 orally; in rats: 1050 orally; in guinea pigs: 47 orally, 19 s.c. (Proske)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
DescriptionPhenformin is an orally administered biguanide derivative with potential to lower blood glucose concentrations in patients with non-insulin-dependent diabetes mellitus. In general, biguanides improve insulin sensitivity and decrease insulin resistance by inhibiting complex 1 of the mitochondrial respiratory chain and inducing AMP-activated protein kinase (AMPK)-dependent signaling. Phenformin, however, has been withdrawn from clinical use because it also inhibits peripheral glucose oxidation and has an associated effect of inducing lactic acidosis when not metabolized sufficiently. Through AMPK activation, phenformin at 300 mg/kg exhibits anticancer activity by inhibiting the growth of MCF-7 and MDAMB231 breast cancer cell xenografts in mice.
Useserectile dysfunction therapy
UsesIt is an anti-diabetic drug from the biguanide class.
General DescriptionWhite solid or powder. Formerly used as an anti-diabetic drug. Toxic (causes lactic acidosis.
Upstream & downstream products
Upstream raw materials
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