guanidine

• ChemBase ID: 418
• Molecular Formular: CH5N3
• Molecular Mass: 59.0705
• Monoisotopic Mass: 59.04834718
• SMILES: NC(=N)N
• Canonical SMILES: NC(=N)N
• InChI: InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
• InChIKey: ZRALSGWEFCBTJO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: guanidine
• IUPAC Traditional name: guanidine
• Brand Name: Guanidine hydrochloride
• Synonyms: Aminomethanamidine; Carbamamidine; Carbamidine; Guanidin; Guanidine Hydrochloride; Guanidinium Chloride; Guanidinium Sulfate; Imidourea; Iminourea; Guanidine

Database IDs

• CAS Number: 113-00-8
• EC Number: 204-021-8
• Beilstein Number: 506044
• PubChem SID: 46507543; 160963881
• PubChem CID: 3520
• CHEBI ID: 42820
• CHEMBL: 821
• Chemspider ID: 3400
• DrugBank ID: DB00536
• Gmelin ID: 100679
• MeSH Name: Guanidine
• Unique Ingredient Identifier: JU58VJ6Y3B
• Wikipedia Title: Guanidine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -3.6522877
• LogD (pH = 7.4): -3.6514976
• Log P: -1.236839
• Molar Refractivity: 25.8588 cm^3
• Polarizability: 5.61125 Å^3
• Polar Surface Area: 75.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.92
• LOG S: -0.71
• Solubility (Water): 1.15e+01 g/l

PROPERTIES

Physical Property

• Solubility: 500 mg/mL (HCl salt)
• Melting Point: 50°C
• Partition Coefficient: -1.251
• Hydrophobicity(logP): -0.6
• Std enthalpy of combustion: -1.0511–-1.0531 MJ mol^-1
• Std enthalpy of formation: -57–-55 kJ mol^-1

Safety Information

• LD50: 475 mg kg^-1 (oral, rat)

Pharmacology Properties

• Half Life: 7–8 hours

DETAILS

DrugBank - DB00536

• Drug Groups: approved
• Description: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC. [PubChem]
• Indication: For the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of Eaton-Lambert. It is not indicated for treating myasthenia gravis.
• Pharmacology: Guanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.
• Toxicity: LD₅₀ = 475 mg/kg (oral, rat). Can cause severe gastrointestinal symptoms (nausea, vomiting and diarrhea), bone marrow suppression, renal insufficiency and other hematologic abnormalities (anemia, leucopenia). Severe guanidine intoxication is characterized by nervous hyperirritability, fibrillary tremors and convulsive contractions of muscle, salivation, vomiting, diarrhea, hypoglycemia, and circulatory disturbances.
• Affected Organisms: Humans and other mammals
• Biotransformation: Not metabolized.
• Absorption: Rapidly absorbed and distributed
• Half Life: 7-8 hours
• External Links: Wikipedia; Drugs.com