guanethidine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antihypertensives, guanidine derivatives 1342 55-65-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • guanethidine
  • abapresin
  • ismelin
  • octatensine
  • oktatensin
  • guanethidine monosulfate
  • guanethidine sulfate
An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.
  • Molecular weight: 198.31
  • Formula: C10H22N4
  • CLOGP: 1.35
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 3
  • TPSA: 65.14
  • ALOGS: -2.29
  • ROTB: 3

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
30 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.20 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 20 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 5, 1960 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC C02CC02 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING
Guanidine derivatives
ATC C02LF01 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
Guanidine derivatives and diuretics
ATC S01EX01 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Other antiglaucoma preparations
MeSH PA D018663 Adrenergic Agents
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:37887 adrenergic antagonist
CHEBI has role CHEBI:66991 sympatholytic agent
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D013565 Sympatholytics

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Anuria contraindication 2472002 DOID:2983
Hypercholesterolemia contraindication 13644009
Secondary angle-closure glaucoma contraindication 21571006
Hypovolemia contraindication 28560003
Dehydration contraindication 34095006
Hyperuricemia contraindication 35885006 DOID:1920
Hypokalemia contraindication 43339004
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Hypochloremic alkalosis contraindication 70134007
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Hypomagnesemia contraindication 190855004
Acute pancreatitis contraindication 197456007 DOID:2913
Neonatal hyperbilirubinemia contraindication 281610001
Azotemia contraindication 445009001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.23 Basic
pKa2 8.7 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent noradrenaline transporter Transporter SUBSTRATE WOMBAT-PK CHEMBL
Alpha-1B adrenergic receptor GPCR WOMBAT-PK
Alpha-1D adrenergic receptor GPCR WOMBAT-PK
Alpha-2C adrenergic receptor GPCR WOMBAT-PK
Alpha-2B adrenergic receptor GPCR WOMBAT-PK
Alpha-1A adrenergic receptor GPCR WOMBAT-PK
Alpha-2A adrenergic receptor GPCR WOMBAT-PK

External reference:

IDSource
D006145 MESH_DESCRIPTOR_UI
4019770 VUID
N0000147861 NUI
C0018318 UMLSCUI
D02237 KEGG_DRUG
5UBY8Y002G UNII
645-43-2 SECONDARY_CAS_RN
79305004 SNOMEDCT_US
5036 RXNORM
387456007 SNOMEDCT_US
d00131 MMSL
4019770 VANDF
004524 NDDF
3518 PUBCHEM_CID
CHEBI:5557 CHEBI
CHEMBL765 ChEMBL_ID
CHEMBL1345 ChEMBL_ID
DB01170 DRUGBANK_ID
1024 INN_ID
CHEMBL2051958 ChEMBL_ID
7194 IUPHAR_LIGAND_ID

Pharmaceutical products:

None