Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H22N4.H2O4S |
| Molecular Weight | 296.387 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.NC(=N)NCCN1CCCCCCC1
InChI
InChIKey=YUFWAVFNITUSHI-UHFFFAOYSA-N
InChI=1S/C10H22N4.H2O4S/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14;1-5(2,3)4/h1-9H2,(H4,11,12,13);(H2,1,2,3,4)
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C10H22N4 |
| Molecular Weight | 198.3085 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Guanethidine belongs to the general class of medicines called antihypertensives. It was used to treat high blood pressure (hypertension). 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. It is taken up by norepinephrine transporters. It becomes concentrated in NE transmitter vesicles, replacing NE in these vesicles.
CNS Activity
Approval Year
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.68 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/374089/ |
160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
GUANETHIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.06 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/374089/ |
80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
GUANETHIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/374089/ |
40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
GUANETHIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/374089/ |
160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
GUANETHIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
650 mg single, oral Studied dose |
unhealthy, 43 years |
|
75 mg 1 times / day multiple, oral Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, 69 years |
Disc. AE: Bradycardia... AEs leading to discontinuation/dose reduction: Bradycardia (extreme, 1 patient) Sources: |
30 mg single, intravenous Dose: 30 mg Route: intravenous Route: single Dose: 30 mg Sources: |
unhealthy |
Disc. AE: Thrombophlebitis, Ischaemia... AEs leading to discontinuation/dose reduction: Thrombophlebitis (1 patient) Sources: Ischaemia (acute, 1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Bradycardia | extreme, 1 patient Disc. AE |
75 mg 1 times / day multiple, oral Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, 69 years |
| Thrombophlebitis | 1 patient Disc. AE |
30 mg single, intravenous Dose: 30 mg Route: intravenous Route: single Dose: 30 mg Sources: |
unhealthy |
| Ischaemia | acute, 1 patient Disc. AE |
30 mg single, intravenous Dose: 30 mg Route: intravenous Route: single Dose: 30 mg Sources: |
unhealthy |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >1000 uM] | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Physiological regulation and NO-dependent inhibition of migrating myoelectric complex in the rat small bowel by OXA. | 2003-10 |
|
| Prejunctional modulation of non-adrenergic non-cholinergic (NANC) inhibitory responses in the isolated guinea-pig gastric fundus. | 2003-06 |
|
| Cytosolic Ca2+ and phosphoinositide hydrolysis linked to constitutively active alpha 1D-adrenoceptors in vascular smooth muscle. | 2003-06 |
|
| Involvement of sympathetic efferents but not capsaicin-sensitive afferents in nociceptin-mediated dual control of rat synovial blood flow. | 2003-06 |
|
| Altered prejunctional modulation of intestinal cholinergic and noradrenergic pathways by alpha2-adrenoceptors in the presence of experimental colitis. | 2003-05 |
|
| Hyperalgesia induced by Asp49 and Lys49 phospholipases A2 from Bothrops asper snake venom: pharmacological mediation and molecular determinants. | 2003-05 |
|
| Intrinsic regulation of CGRP release by dental pulp sympathetic fibers. | 2003-05 |
|
| Short-chain fatty acids stimulate colonic transit via intraluminal 5-HT release in rats. | 2003-05 |
|
| Distribution of vasoactive intestinal polypeptide in the rat heart: effect of guanethidine and capsaicin. | 2003-04 |
|
| Effects of NCX 4050, a new NO donor, in rabbit and human corpus cavernosum. | 2003-04 |
|
| [Pharmacological sympathetic block in complex regional pain syndrome]. | 2003-03-21 |
|
| [Therapeutic approach to complex regional pain syndrome]. | 2003-03-21 |
|
| Investigation of the mechanism of nicotine-induced relaxation in guinea pig gallbladder. | 2003-03 |
|
| Chemical sympathectomy-induced changes in TH-, VIP-, and CGRP-immunoreactive fibers in the rat mandible periosteum: influence on bone resorption. | 2003-03 |
|
| Involvement of a purinergic pathway in the sympathetic regulation of motility in rat ileum. | 2003-02-28 |
|
| [Diagnose Sudeck's disease in good time and save your patient from martyrdom]. | 2003-02-27 |
|
| Functional evidence for a role of GABA receptors in modulating nerve activities of circular smooth muscle from rat colon in vitro. | 2003-02-14 |
|
| Ketamine and midazolam differentially inhibit nonadrenergic noncholinergic lower esophageal sphincter relaxation in rabbits: role of superoxide anion and nitric oxide synthase. | 2003-02 |
|
| Role of opioid and nitric oxide systems in the nonadrenergic noncholinergic-mediated relaxation of corpus cavernosum in bile duct-ligated rats. | 2003-01-24 |
|
| Study of the mechanisms involved in the bradykinin-induced contraction of the pig iris sphincter muscle in vitro. | 2003-01-01 |
|
| Neural mechanism of acupuncture-induced gastric relaxations in rats. | 2003-01 |
|
| Pharmacological evidence that tetraethylammonium-sensitive, iberiotoxin-insensitive K+ channels function as a negative feedback element for sympathetic neurotransmission by suppressing omega-conotoxin-GVIA-insensitive Ca2+ channels in the relaxation of rabbit facial vein. | 2003-01 |
|
| Characterization of the 5-hydroxytryptamine receptors mediating contraction in the pig isolated intravesical ureter. | 2003-01 |
|
| Influence of nitric oxide on neurogenic contraction and relaxation of the human gastroepiploic artery. | 2003-01 |
|
| Mechanisms of excitatory transmission in circular smooth muscles of the guinea pig seminal vesicle. | 2003-01 |
|
| The effect of chemical sympathectomy on the conducting system of the white rat vagus nerve. | 2002-12-10 |
|
| Excitatory motor innervation in the canine rectoanal region: role of changing receptor populations. | 2002-12 |
|
| Involvement of peptide histidine isoleucine in non-adrenergic non-cholinergic relaxation of the rat gastric fundus induced by high-frequency neuronal firing. | 2002-12 |
|
| The beneficial effects of protein tyrosine kinase inhibition on the circulatory failure induced by endotoxin in the rat. | 2002-11 |
|
| The effect of guanethidine and local anesthetics on the electrically stimulated mouse vas deferens. | 2002-11 |
|
| Purines and pyrimidines are not involved in NANC relaxant responses in the rabbit vaginal wall. | 2002-10 |
|
| Anesthetic pain management in Siriraj Hospital: a retrospective review. | 2002-09 |
|
| Additional evidence that the sympathetic nervous system regulates the vessel wall release of tissue plasminogen activator. | 2002-09 |
|
| Cholinergic and nitrergic regulation of in vivo giant migrating contractions in rat colon. | 2002-09 |
|
| Characterisation of a modified approach to the study of sympathetic neurotransmission and its presynaptic modulation in the isolated rabbit thoracic aorta. | 2002-08-17 |
|
| Rebound contraction by nitric oxide in the longitudinal muscle of porcine gastric fundus. | 2002-08 |
|
| Pharmacology and thermosensitivity of the dartos muscle isolated from rat scrotum. | 2002-08 |
|
| Sympathetic-renal interaction in chronic arterial pressure control. | 2002-08 |
|
| Alpha7-nicotinic acetylcholine receptors on cerebral perivascular sympathetic nerves mediate choline-induced nitrergic neurogenic vasodilation. | 2002-07-12 |
|
| Effects of GABA on circular smooth muscle spontaneous activities of rat distal colon. | 2002-07-12 |
|
| Chemical sympathectomy alters food intake and thermogenic responses to catecholamines in rats. | 2002-07-05 |
|
| Effects of guanethidine administration on compensatory ovarian hypertrophy, compensatory ovulation and follicular development in the prepubertal female guinea pig. | 2002-07 |
|
| Effects of functional peripheral sympathetic denervation induced by guanethidine on follicular development and ovulation of the adult female guinea pig. | 2002-07 |
|
| Bradykinin is involved in hyperalgesia induced by Bothrops jararaca venom. | 2002-07 |
|
| Role of Ca2+-activated Cl- channels and MLCK in slow IJP in opossum esophageal smooth muscle. | 2002-07 |
|
| Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1. | 2002-05 |
|
| [Colorful pain]. | 2002 |
|
| Effects of ecabet sodium, an antiulcer drug, on gastric adaptive relaxation in isolated guinea-pig stomachs. | 2002 |
|
| Influence of Helicobacter pylori infection on in vitro responsiveness of gastric fundus to agonists and to stimulation of enteric nerves in Mongolian gerbils. | 2002 |
|
| Factors predisposing to postural hypotensive symptoms in the treatment of high blood pressure. | 1975-10 |
Patents
Sample Use Guides
For high blood pressure: Adults—at first, 10 or 12.5 milligrams (mg) once a day. Then, your doctor may increase your dose to 25 to 50 mg once a day. Children: the dose is based on body weight and must be determined by your doctor. The usual dose is 200 micrograms (mcg) per kilogram (kg) (90.9 mcg per pound) of body weight a day.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: It was studied the effect of guanethidine on the alpha-adrenoceptor blocking potency of phentolamine using the rabbit aortic strip and rat vas deferens. The agonists used were and. Guanethidine augmented the responses to noradrenaline and xylometazoline and increased the pA2 value of phentolamine against both agonists. Increased affinity of alpha-receptors may be partly responsible for the guanethidine-induced supersensitivity to alpha-adrenoceptor agonists.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:45:31 GMT 2025
by
admin
on
Mon Mar 31 18:45:31 GMT 2025
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| Record UNII |
5UBY8Y002G
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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FDA ORPHAN DRUG |
6385
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NCI_THESAURUS |
C270
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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51016
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m5865
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86471
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645-43-2
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CHEMBL765
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1301801
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211-442-0
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100000080182
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C65831
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DTXSID20110019
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SUB12005MIG
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5UBY8Y002G
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82023
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DB01170
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