TRIMETHAPHAN CAMSYLATE

Details

Stereochemistry	MIXED
Molecular Formula	C22H25N2OS.C10H15O4S
Molecular Weight	596.8
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@@H]2CC[C@@]1(CS([O-])(=O)=O)C(=O)C2.O=C3N(CC4=CC=CC=C4)C5C[S+]6CCCC6C5N3CC7=CC=CC=C7

InChI

InChIKey=HALWUDBBYKMYPW-STOWLHSFSA-M

InChI=1S/C22H25N2OS.C10H16O4S/c25-22-23(14-17-8-3-1-4-9-17)19-16-26-13-7-12-20(26)21(19)24(22)15-18-10-5-2-6-11-18;1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h1-6,8-11,19-21H,7,12-16H2;7H,3-6H2,1-2H3,(H,12,13,14)/q+1;/p-1/t;7-,10-/m.1/s1

HIDE SMILES / InChI

Molecular Formula	C10H15O4S
Molecular Weight	231.289
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C22H25N2OS
Molecular Weight	365.512
Charge	1
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/mmx/trimethaphan-camsylate.html | https://www.ncbi.nlm.nih.gov/pubmed/8618259

Trimethaphan (or Trimethaphan camsylate), a ganglionic blocking agent and an antihypertensive drug, was marketed under the brand name Arfonad. Arfonad is indicated to induce systemic arterial hypotension in patients undergoing major surgery and to treat severe systemic hypertension, and in the emergency treatment of pulmonary edema in patients with pulmonary hypertension associated with systemic hypertension. Trimethaphan prevents stimulation of postsynaptic receptors by competing with acetylcholine for these receptor sites. Additional effects may include direct peripheral vasodilation and release of histamine. This drug was discontinued because of the competition from newer drugs that are more selective in their actions and effects.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=008983	Primary		Approved 8429	ARFONAD Approved Use Hypotension, controlled (induction and maintenance) - Trimethaphan is indicated for production of controlled hypotension during surgery to reduce bleeding into the surgical field. Hypertension (treatment) - Trimethaphan is indicated for rapid reduction of blood pressure in the treatment of hypertensive emergencies, especially in patients with acute dissecting aneurysm, and in the emergency treatment of pulmonary edema in patients with pulmonary hypertension associated with systemic hypertension.

Doses

Dose	Population	Adverse events
9 mg/min 1 times / day multiple, intravenous (mean) Studied dose Dose: 9 mg/min, 1 times / day Route: intravenous Route: multiple Dose: 9 mg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/938175/	unhealthy, 23 to 66 years n = 4 Health Status: unhealthy Condition: hypertension Age Group: 23 to 66 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/938175/	Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest Sources: https://pubmed.ncbi.nlm.nih.gov/938175/
0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	Other AEs: Yawning, Sensation of warmth... Other AEs: Yawning Sensation of warmth Nausea Vomiting Pallor Dizziness Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/

AEs

AE	Significance	Dose	Population
Respiratory arrest	Disc. AE	9 mg/min 1 times / day multiple, intravenous (mean) Studied dose Dose: 9 mg/min, 1 times / day Route: intravenous Route: multiple Dose: 9 mg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/938175/	unhealthy, 23 to 66 years n = 4 Health Status: unhealthy Condition: hypertension Age Group: 23 to 66 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/938175/
Dizziness		0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Nausea		0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Pallor		0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Sensation of warmth		0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Vomiting		0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Yawning		0.115 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2MN5
ABI Chem	AC1Q6LI1
Alfa Chemistry	ACM68917
BOC Sciences	21035-85-8
BOC Sciences	68-91-7
BOC Sciences	7187-66-8
ChemMol	99147727	http://www.chemmol.com/chemmol/99147727.html
Compound Cloud	23576
Compound Cloud	441310
MuseChem	I009884
MuseChem	M019330
THE BioTek	bt-425772	https://www.thebiotek.com/product/others/bt-425772
Tetrahedron	TS74953
Toronto Research Chemicals	T344755
Toronto Research Chemicals	T795435
ZINC	ZINC000003831581	http://zinc15.docking.org/substances/ZINC000003831581
ZINC	ZINC000003938748	http://zinc15.docking.org/substances/ZINC000003938748
ZINC	ZINC000100308855	http://zinc15.docking.org/substances/ZINC000100308855
ZINC	ZINC000100308860	http://zinc15.docking.org/substances/ZINC000100308860
ZINC	ZINC000207869944	http://zinc15.docking.org/substances/ZINC000207869944
eMolecules	110042105
eMolecules	313119497
eNovation Chemicals	D673675	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673675

PubMed

Title	Date	PubMed
Pyramidal tract responses (PTR) during hypoxia and hypotension.	1976 Sep-Oct	960174
Selective osmoreceptor dysfunction in the syndrome of chronic hypernatremia.	1977 Apr	849975
Canine systemic and cerebral effects of hypotension induced by hemorrhage, trimethaphan, halothane, or nitroprusside.	1977 Mar	842872
[Electrocardiographic changes observed during the use of trimethaphan in the treatment of malignant arterial hypertension].	1978 Aug	727981
Postischemic brain oxygenation with barbiturate therapy in rats.	1979 Aug	37043
Cerebral energy levels during trimethaphan-induced hypotension in the rat: effects of light versus deep halothane anesthesia.	1979 Jan	760601
Prolonged apnea following trimethaphan and succinylcholine.	1979 Jan	216287
[A comparison of the metabolic effects of hypotension induced by arteriotomy, trimethaphan, nitroprusside, or deep halothane in dog (author's transl)].	1981 Sep	7328742
[The effects of controlled hypotension induced by prostaglandin E1 and trimethaphan on coronary and systemic hemodynamics and myocardial contractility (author's transl)].	1982 Apr	7202062
Cerebral and systemic effects of hypotension induced by trimetaphan or nitroprusside in dogs.	1982 Dec	7158277
Autoregulation of myocardial blood flow under controlled hypotension in the dog.	1982 Jun	7113627
Trimethaphan-induced hypotension: effect on renal function.	1982 Nov	7139398
Altered osmotic threshold for vasopressin release and impaired thirst sensation: additional abnormalities in Kallmann's syndrome.	1982 Oct	7107821
Profound arterial hypotension in dogs: brain electrical activity and organ integrity.	1983 Jan	6848019
[Difference in susceptibility between auditory and equilibrium function in rabbits with experimentally-induced transient ischemic attack].	1989 Feb	2746423
Acute left bundle branch block precipitated by trimethaphan.	1989 Sep	2774249
Chronic lesion of rostral ventrolateral medulla in spontaneously hypertensive rats.	1992 Feb	1735570
Effects of ischemia duration on neurological outcome, CA1 histopathology, and nonmatching to sample learning in monkeys.	1992 Oct	1412584
Cerebral blood flow distribution during induced hypotension with haemorrhage, trimetaphan or nitroprusside in rats.	1995 Jun	7640125
Differential microcirculation dynamics during deliberate hypotension induced by nicardipine, PGE1 and trimethaphan in rat mesentery.	1995 Nov	8590494
Trimetaphan may cause coronary artery spasm.	1995 Sep	8542864

Patents

Sample Use Guides

In Vivo Use Guide

Controlled hypotension during surgery: Initial: Intravenous infusion, 3 to 4 mg per minute, adjusted according to response. Maintenance: Intravenous infusion, 300 mcg (0.3 mg) to 6 mg per minute. Hypertensive emergency: Initial: Intravenous infusion, 500 mcg (0.5 mg) to 1 mg per minute, adjusted according to response. Maintenance: Intravenous infusion, 1 to 5 mg per minut

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:25:52 GMT 2023` Edited by `admin` on `Fri Dec 15 16:25:52 GMT 2023`
Record UNII	8W556014K9
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRIMETHAPHAN CAMSYLATE

Common Name

English

ARFONAD

Brand Name

English

THIENO(1',2':1,2)THIENO(3,4-D)IMIDAZOL-5-IUM, DECAHYDRO-2-OXO-1,3-BIS(PHENYLMETHYL)-, SALT WITH (+)-7,7-DIMETHYL-2-OXOBICYCLO(2.2.1)HEPTANE-1-METHANESULFONIC ACID (1:1)

Common Name

English

TRIMETAPHAN CAMSILATE [JAN]

Common Name

English

TRIMETHAPHAN CAMSYLATE [ORANGE BOOK]

Common Name

English

Trimetaphan camsilate [WHO-DD]

Common Name

English

TRIMETAPHAN CAMSYLATE

Common Name

English

TRIMETHAPHAN CAMSYLATE [MI]

Common Name

English

TRIMETAPHAN CAMSILATE

Official Name

English

(+)-1,3-DIBENZYLDECAHYDRO-2-OXOIMIDAZO(4,5-C)THIENO(1,2-A)-THIOLIUM 2-OXO-10-BORNANESULFONATE (1:1)

Systematic Name

English

NU-2222

Code

English

trimetaphan camsilate [INN]

Common Name

English

TRIMETAPHAN CAMSILATE [MART.]

Common Name

English

TRIMETHAPHAN CAMSYLATE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270