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Identification
NameGuanidine
Accession NumberDB00536  (APRD01008, EXPT01546)
TypeSmall Molecule
GroupsApproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
AminomethanamidineNot AvailableNot Available
GuNot AvailableNot Available
GuanidinNot AvailableNot Available
GUANIDINENot AvailableNot Available
H2N-C(=NH)-NH2Not AvailableNot Available
ImidoureaNot AvailableNot Available
IminoureaNot AvailableNot Available
Salts
Name/CAS Structure Properties
Guanidine hydrochloride
Thumb
  • InChI Key: PJJJBBJSCAKJQF-UHFFFAOYSA-N
  • Monoisotopic Mass: 95.025024914
  • Average Mass: 95.531
DBSALT000737
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number113-00-8
WeightAverage: 59.0705
Monoisotopic: 59.048347175
Chemical FormulaCH5N3
InChI KeyZRALSGWEFCBTJO-UHFFFAOYSA-N
InChI
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
IUPAC Name
guanidine
SMILES
NC(N)=N
Mass Specshow(8.28 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassGuanidines
SubclassNot Available
Direct parentGuanidines
Alternative parentsPolyamines; Amidines
Substituentsamidine; polyamine; amine
Classification descriptionThis compound belongs to the guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
Pharmacology
IndicationFor 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.
PharmacodynamicsGuanidine 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.
Mechanism of actionNot Available
AbsorptionRapidly absorbed and distributed
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Not metabolized.

Route of eliminationNot Available
Half life7-8 hours
ClearanceNot Available
ToxicityLD50 = 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9378
Blood Brain Barrier + 0.8502
Caco-2 permeable - 0.7527
P-glycoprotein substrate Non-substrate 0.8033
P-glycoprotein inhibitor I Non-inhibitor 0.977
P-glycoprotein inhibitor II Non-inhibitor 0.932
Renal organic cation transporter Non-inhibitor 0.7825
CYP450 2C9 substrate Non-substrate 0.8402
CYP450 2D6 substrate Non-substrate 0.6619
CYP450 3A4 substrate Non-substrate 0.8447
CYP450 1A2 substrate Non-inhibitor 0.9843
CYP450 2C9 substrate Non-inhibitor 0.9588
CYP450 2D6 substrate Non-inhibitor 0.9695
CYP450 2C19 substrate Non-inhibitor 0.9772
CYP450 3A4 substrate Non-inhibitor 0.9763
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9789
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.7148
Biodegradation Not ready biodegradable 0.7652
Rat acute toxicity 1.9367 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9733
hERG inhibition (predictor II) Non-inhibitor 0.9798
Pharmacoeconomics
Manufacturers
  • Schering corp
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Guanidine hcl 125 mg tablet0.25USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point50 °CPhysProp
water solubility1840 mg/L (at 20 °C)GREENWALD,I (1926)
logP-0.6Not Available
pKa12.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.5ALOGPS
logP-1.9ALOGPS
logP-1.2ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)12.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.89 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.86 m3·mol-1ChemAxon
Polarizability5.57 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MS
References
Synthesis Reference

Helmut Hoffmann, Carlhans Suling, “Process for the production of guanidine salts of aliphatic mercaptosulphonic acids.” U.S. Patent US3956368, issued November, 1954.

US3956368
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound3520
PubChem Substance46507543
ChemSpider3400
ChEBI24435
ChEMBLCHEMBL821
PharmGKBPA164781028
HETGAI
Drugs.comhttp://www.drugs.com/mtm/guanidine.html
WikipediaGuanidine
ATC CodesA07AB03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72.9 KB)
Interactions
Drug Interactions
Drug
TacrineThe acetylcholinesterase inhibitor, Tacrine, may increase the adverse/toxic effects of Guanidine, a cholinergic agonist. Monitor for increased cholinergic effects and toxicity.
Food InteractionsNot Available

Targets

1. Argininosuccinate synthase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Argininosuccinate synthase P0A6E4 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Guanidinoacetate N-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Guanidinoacetate N-methyltransferase Q14353 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Komoto J, Yamada T, Takata Y, Konishi K, Ogawa H, Gomi T, Fujioka M, Takusagawa F: Catalytic mechanism of guanidinoacetate methyltransferase: crystal structures of guanidinoacetate methyltransferase ternary complexes. Biochemistry. 2004 Nov 16;43(45):14385-94. Pubmed
  4. Karelin AA, Mardashev SR: [The stimulating effect of cyclic AMP, glucagon and insulin on guanidine acetate-N-methyltransferase activity in rat liver and pancreas] Biokhimiia. 1976 Feb;41(2):316-23. Pubmed
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Ribonuclease pancreatic

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ribonuclease pancreatic P07998 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Dodge RW, Laity JH, Rothwarf DM, Shimotakahara S, Scheraga HA: Folding pathway of guanidine-denatured disulfide-intact wild-type and mutant bovine pancreatic ribonuclease A. J Protein Chem. 1994 May;13(4):409-21. Pubmed
  4. Nasiri H, Forouzandeh M, Rasaee MJ, Rahbarizadeh F: Modified salting-out method: high-yield, high-quality genomic DNA extraction from whole blood using laundry detergent. J Clin Lab Anal. 2005;19(6):229-32. Pubmed
  5. Loh SN, Rohl CA, Kiefhaber T, Baldwin RL: A general two-process model describes the hydrogen exchange behavior of RNase A in unfolding conditions. Proc Natl Acad Sci U S A. 1996 Mar 5;93(5):1982-7. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. Disks large homolog 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Disks large homolog 4 P78352 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

6. Lysozyme

Kind: protein

Organism: Enterobacteria phage T4

Pharmacological action: unknown

Components

Name UniProt ID Details
Lysozyme P00720 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Junn HJ, Youn J, Suh KH, Lee SS: Cloning and expression of Klebsiella phage K11 lysozyme gene. Protein Expr Purif. 2005 Jul;42(1):78-84. Epub 2005 Apr 19. Pubmed
  4. Garcia-Orozco KD, Lopez-Zavala AA, Puentes-Camacho D, Calderon-de-la-Barca AM, Sotelo-Mundo RR: Recombinant bacterial expression of the lysozyme from the tobacco-hornworm Manduca sexta with activity at low temperatures. Biotechnol Lett. 2005 Aug;27(15):1075-80. Pubmed
  5. Shiraki K, Kudou M, Sakamoto R, Yanagihara I, Takagi M: Amino Acid esters prevent thermal inactivation and aggregation of lysozyme. Biotechnol Prog. 2005 Mar-Apr;21(2):640-3. Pubmed

7. Aldehyde dehydrogenase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Aldehyde dehydrogenase, mitochondrial P05091 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Arginase

Kind: protein

Organism: Bacillus caldovelox

Pharmacological action: unknown

Components

Name UniProt ID Details
Arginase P53608 Details

Transporters

1. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

References:

  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. Pubmed
  2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. Pubmed
  3. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. Pubmed
  4. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. Pubmed
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. Pubmed
  2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. Pubmed
  3. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. Pubmed

3. Solute carrier family 22 member 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 3 O75751 Details

References:

  1. Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. Pubmed
  2. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. Pubmed

4. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

References:

  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. Pubmed
  2. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. Pubmed
  3. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. Pubmed
  4. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. Pubmed

5. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. Pubmed

6. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

References:

  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11