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)
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 |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
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 n = 1 Health Status: unhealthy Age Group: 43 years Population Size: 1 Sources: |
|
75 mg 1 times / day multiple, oral Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Co-administed with:: furosemide(40 mg twice daily) Sources: |
unhealthy, 69 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 69 years Sex: M Population Size: 1 Sources: |
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 n = 120 Health Status: unhealthy Condition: algodystrophy Sex: M+F Population Size: 120 Sources: |
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 Co-administed with:: furosemide(40 mg twice daily) Sources: |
unhealthy, 69 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 69 years Sex: M Population Size: 1 Sources: |
| Thrombophlebitis | 1 patient Disc. AE |
30 mg single, intravenous Dose: 30 mg Route: intravenous Route: single Dose: 30 mg Sources: |
unhealthy n = 120 Health Status: unhealthy Condition: algodystrophy Sex: M+F Population Size: 120 Sources: |
| Ischaemia | acute, 1 patient Disc. AE |
30 mg single, intravenous Dose: 30 mg Route: intravenous Route: single Dose: 30 mg Sources: |
unhealthy n = 120 Health Status: unhealthy Condition: algodystrophy Sex: M+F Population Size: 120 Sources: |
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 |
|---|---|---|
| Factors predisposing to postural hypotensive symptoms in the treatment of high blood pressure. | 1975 Oct |
|
| Paeoniflorin reverses guanethidine-induced hypotension via activation of central adenosine A1 receptors in Wistar rats. | 1999 Oct |
|
| Co-transmitter function of ATP in central catecholaminergic neurons of the rat. | 2001 |
|
| Contribution of alpha(2) receptor subtypes to nerve injury-induced pain and its regulation by dexmedetomidine. | 2001 Apr |
|
| KT3-671, an angiotensin AT1 receptor antagonist, attenuates vascular but not cardiac responses to sympathetic nerve stimulation in pithed rats. | 2001 Apr |
|
| Voltage-operated Ca(2+) channels involved in K(+)-evoked release of vasoactive intestinal polypeptide from the rat hypothalamus. | 2001 Apr |
|
| Modulation of nitrergic relaxant responses by peptides in the mouse gastric fundus. | 2001 Apr 2 |
|
| The role of nitric oxide in mediating nonadrenergic, noncholinergic relaxation in rat pulmonary artery. | 2001 Aug |
|
| Degeneration of capsaicin-sensitive sensory nerves leads to increased salt sensitivity through enhancement of sympathoexcitatory response. | 2001 Feb |
|
| Contractile effects and intracellular Ca2+ signalling induced by motilin and erythromycin in the circular smooth muscle of human colon. | 2001 Feb |
|
| Respiratory effects of stimulation of cell bodies of the A5 region in the anaesthetised rat. | 2001 Jan |
|
| Neurophysiological basis for neurogenic-mediated articular cartilage anabolism alteration. | 2001 Jan |
|
| Correlation between the release of the sympathetic neurotransmitter ATP and soluble nucleotidases from the guinea pig vas deferens. | 2001 Jan |
|
| The effect of superoxide dismutase on nitric oxide-mediated and electrical field-stimulated diabetic rabbit cavernosal smooth muscle relaxation. | 2001 Jan |
|
| Intravenous anesthetics inhibit nonadrenergic noncholinergic lower esophageal sphincter relaxation via nitric oxide-cyclic guanosine monophosphate pathway modulation in rabbits. | 2001 Jul |
|
| Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum. | 2001 Jun |
|
| Treatment of reflex sympathetic dystrophy (CRPS type 1): a research synthesis of 21 randomized clinical trials. | 2001 Jun |
|
| Mechanism of internal anal sphincter smooth muscle relaxation by phorbol 12,13-dibutyrate. | 2001 Jun |
|
| Gastric distension-induced pyloric relaxation: central nervous system regulation and effects of acute hyperglycaemia in the rat. | 2001 Jun 15 |
|
| Advanced glycation end-products are responsible for the impairment of corpus cavernosal smooth muscle relaxation seen in diabetes. | 2001 Mar |
|
| Combination of phentolamine and L-arginine or sildenafil synergistically improves neurogenic relaxation of rabbit corpus cavernosum smooth muscle. | 2001 Mar |
|
| Possible role of orexin A in nonadrenergic, noncholinergic inhibitory response of muscle of the mouse small intestine. | 2001 Oct 12 |
|
| [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 |
|
| Generalized loss of inhibitory innervation reverses serotonergic inhibition into excitation in a rabbit model of TNBS-colitis. | 2002 Apr |
|
| Rebound contraction by nitric oxide in the longitudinal muscle of porcine gastric fundus. | 2002 Aug |
|
| Pharmacology and thermosensitivity of the dartos muscle isolated from rat scrotum. | 2002 Aug |
|
| Sympathetic-renal interaction in chronic arterial pressure control. | 2002 Aug |
|
| Potentiation of motilin-induced contraction by nitric oxide synthase inhibition in the isolated chicken gastrointestinal tract. | 2002 Feb |
|
| Presynaptic modulation of cholinergic neurotransmission in the human proximal stomach. | 2002 Jan |
|
| Bradykinin is involved in hyperalgesia induced by Bothrops jararaca venom. | 2002 Jul |
|
| Noradrenaline, infused locally, reduces arrhythmia severity during coronary artery occlusion in anaesthetised dogs. | 2002 Jul |
|
| The effect of chemical sympathectomy on the conducting system of the white rat vagus nerve. | 2002 Jul-Aug |
|
| Effects of infantile/prepubertal chronic estrogen treatment and chemical sympathectomy with guanethidine on developing cholinergic nerves of the rat uterus. | 2002 Jun |
|
| Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1. | 2002 May |
|
| Stimulatory effect of paeoniflorin on the release of noradrenaline from ileal synaptosomes of guinea-pig in-vitro. | 2002 May |
|
| The beneficial effects of protein tyrosine kinase inhibition on the circulatory failure induced by endotoxin in the rat. | 2002 Nov |
|
| The effect of guanethidine and local anesthetics on the electrically stimulated mouse vas deferens. | 2002 Nov |
|
| Cholinergic and nitrergic regulation of in vivo giant migrating contractions in rat colon. | 2002 Sep |
|
| Effects of NCX 4050, a new NO donor, in rabbit and human corpus cavernosum. | 2003 Apr |
|
| Ketamine and midazolam differentially inhibit nonadrenergic noncholinergic lower esophageal sphincter relaxation in rabbits: role of superoxide anion and nitric oxide synthase. | 2003 Feb |
|
| Neural mechanism of acupuncture-induced gastric relaxations in rats. | 2003 Jan |
|
| Role of opioid and nitric oxide systems in the nonadrenergic noncholinergic-mediated relaxation of corpus cavernosum in bile duct-ligated rats. | 2003 Jan 24 |
|
| Prejunctional modulation of non-adrenergic non-cholinergic (NANC) inhibitory responses in the isolated guinea-pig gastric fundus. | 2003 Jun |
|
| Investigation of the mechanism of nicotine-induced relaxation in guinea pig gallbladder. | 2003 Mar |
|
| Hyperalgesia induced by Asp49 and Lys49 phospholipases A2 from Bothrops asper snake venom: pharmacological mediation and molecular determinants. | 2003 May |
|
| Short-chain fatty acids stimulate colonic transit via intraluminal 5-HT release in rats. | 2003 May |
|
| Physiological regulation and NO-dependent inhibition of migrating myoelectric complex in the rat small bowel by OXA. | 2003 Oct |
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
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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FDA ORPHAN DRUG |
6385
Created by
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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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PRIMARY | Merck Index | ||
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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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ACTIVE MOIETY
SUBSTANCE RECORD
