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
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
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 |
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 |
---|---|---|---|---|
Primary | ARFONAD Approved UseHypotension, 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: |
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: |
Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest Sources: |
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
Other AEs: Yawning, Sensation of warmth... Other AEs: Yawning Sources: Sensation of warmth Nausea Vomiting Pallor Dizziness |
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: |
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: |
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
|
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
|
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
|
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
|
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
|
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: |
pregnant, adult n = 56 Health Status: pregnant Age Group: adult Sex: F Population Size: 56 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[The effects of sodiumnitroprusside and trimethaphan induced hypotension on haemodynamics and myocardial oxygen consumption (author's transl)]. | 1976 Jan |
|
Pyramidal tract responses (PTR) during hypoxia and hypotension. | 1976 Sep-Oct |
|
Canine systemic and cerebral effects of hypotension induced by hemorrhage, trimethaphan, halothane, or nitroprusside. | 1977 Mar |
|
[Electrocardiographic changes observed during the use of trimethaphan in the treatment of malignant arterial hypertension]. | 1978 Aug |
|
Postischemic brain oxygenation with barbiturate therapy in rats. | 1979 Aug |
|
[Use of methoxamine in trimethaphan-induced hypotension]. | 1979 Jan |
|
Prolonged apnea following trimethaphan and succinylcholine. | 1979 Jan |
|
Brain blood flow and metabolism after global ischemia and post-insult thiopental therapy in monkeys. | 1979 Sep-Oct |
|
[The effects of controlled hypotension induced by prostaglandin E1 and trimethaphan on coronary and systemic hemodynamics and myocardial contractility (author's transl)]. | 1982 Apr |
|
Cerebral and systemic effects of hypotension induced by trimetaphan or nitroprusside in dogs. | 1982 Dec |
|
Autoregulation of myocardial blood flow under controlled hypotension in the dog. | 1982 Jun |
|
Trimethaphan-induced hypotension: effect on renal function. | 1982 Nov |
|
Altered osmotic threshold for vasopressin release and impaired thirst sensation: additional abnormalities in Kallmann's syndrome. | 1982 Oct |
|
Changes in cardiac output and systemic arterial pressure after insertion of acrylic cement during trimetaphan, sodium nitroprusside and glycerol trinitrate-induced hypotension. A comparison with changes during normotension. | 1983 Aug |
|
Hemodynamics and myocardial metabolism under deliberate hypotension. An experimental study in dogs. | 1983 Dec |
|
[Effect of hypotension induced by trimethaphan and nitroglycerin on intraocular pressure in man]. | 1983 Feb |
|
Profound arterial hypotension in dogs: brain electrical activity and organ integrity. | 1983 Jan |
|
Regional blood flows during induced hypotension produced by nitroprusside or trimethaphan in the rhesus monkey. | 1985 Aug |
|
The influence of trimethaphan (Arfonad)-induced hypotension with and without spine distraction on canine spinal cord blood flow. | 1986 Apr |
|
[Effect of trimethaphan-induced hypotension on pituitary-adrenocortical function]. | 1986 Mar |
|
[Effect of trimethaphan-induced hypotension on carbohydrate metabolism]. | 1986 Oct |
|
The effect of trimethaphan-induced hypotension on canine spinal cord blood flow. Measurement at different cord levels using radiolabelled microspheres. | 1988 May |
|
[Difference in susceptibility between auditory and equilibrium function in rabbits with experimentally-induced transient ischemic attack]. | 1989 Feb |
|
Acute left bundle branch block precipitated by trimethaphan. | 1989 Sep |
|
The hemodynamic and metabolic changes in prostaglandin E1-induced hypotension in dogs--a comparative study with trimetaphan-induced hypotension. | 1989 Sep 1 |
|
[Baroreceptor reflex response to acute blood loss during induced hypotension--a comparison of sodium nitroprusside, prostaglandin E1 and trimethaphan]. | 1990 May |
|
Chronic lesion of rostral ventrolateral medulla in spontaneously hypertensive rats. | 1992 Feb |
|
[Effects of induced hypotensive anesthesia on the blood coagulation-fibrinolysis system measured by thrombelastography--comparison between prostaglandin E1 and trimethaphan]. | 1992 Jan |
|
[Pharmacokinetics of epidurally administered bupivacaine during prostaglandin E1- or trimetaphan-induced hypotension]. | 1992 May |
|
Effects of ischemia duration on neurological outcome, CA1 histopathology, and nonmatching to sample learning in monkeys. | 1992 Oct |
|
Epidural blood flow during prostaglandin E1 or trimethaphan induced hypotension. | 1993 Nov |
|
Epidural blood flow during prostaglandin E1 or trimethaphan induced hypotension. | 1994 Apr |
|
[Effect of deliberate hypotension on renal functions during epidural block plus inhalation anesthesia: a comparison of prostaglandin E1 and trimethaphan]. | 1994 Oct |
|
Differential microcirculation dynamics during deliberate hypotension induced by nicardipine, PGE1 and trimethaphan in rat mesentery. | 1995 Nov |
|
Trimetaphan may cause coronary artery spasm. | 1995 Sep |
|
Effects of trimetaphan-induced deliberate hypotension on human cochlear blood flow. | 1998 |
|
Cerebral blood-flow responses to induced hypotension and to CO2 inhalation in patients with major cerebral artery occlusive disease: a positron-emission tomography study. | 1999 Feb |
|
Role of the multidomain protein spinophilin in blood pressure and cardiac function regulation. | 2008 Oct |
Patents
Sample Use Guides
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
Edited
Fri Dec 15 16:25:52 UTC 2023
by
admin
on
Fri Dec 15 16:25:52 UTC 2023
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Record UNII |
8W556014K9
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C270
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NCI_THESAURUS |
C66886
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100000076923
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Trimetaphan camsilate
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SUB11305MIG
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38680
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C66639
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9729
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DBSALT001381
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200-696-8
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44602409
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DTXSID3023710
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68-91-7
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296
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8W556014K9
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CHEMBL1201329
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C017774
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m11146
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PRIMARY | Merck Index |
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