Tripamide

Tripamide
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name 3-(aminosulfonyl)-4-chloro-N-[(3aR,4S,7R,7aS)-octahydro-2H-4,7-methanoisoindol-2-yl]benzamide
CAS Number	73803-48-2
PubChem (CID)	636401
UNII	G36A0E9CVT^Y
ChEMBL	CHEMBL2104484
Chemical and physical data
Formula	C₁₆H₂₀ClN₃O₃S
Molar mass	369.86
3D model (Jmol)	Interactive image
SMILES C1C[C@@H]2C[C@H]1[C@@H]3[C@H]2CN(C3)NC(=O)C4=CC(=C(C=C4)Cl)S(=O)(=O)N
(verify)

Tripamide (INN) is a diuretic.

Synthesis

Tripamide synthesis:^[1]

Preparation starts by exhaustive reduction of the Diels-Alder adduct from cyclopentadiene and maleimide (1). Nitrosation of the product (2), followed by reduction of the nitroso group of 3, gives the corresponding hydrazine (4). Acylation with acid chloride 5 gives tripamide (6).

References

↑ U.S. Patent 3,787,440

Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂ agonist	Clonidine Guanabenz Guanfacine Methyldopa^# Tiamenidine^‡

Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guanethidine Guanoclor Guanazodine Guanoxabenz Guanoxan

Imidazoline receptor agonist	Moxonidine Rilmenidine Tolonidine

Ganglion-blocking/nicotinic antagonist	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

MAOI	Pargyline^‡

Adrenergic uptake inhibitor	Bietaserpine Deserpidine Methoserpidine Rescinnamine Reserpine

Tyrosine hydroxylase inhibitor	Metirosine

Direct

α₁ blockers	Prazosin Indoramin Trimazosin Doxazosin Urapidil

Non-selective α blocker	Phentolamine

Other antagonists

Serotonin antagonist	Ketanserin Lidanserin

Endothelin antagonist (for PH)	dual (Bosentan, Macitentan) selective (Ambrisentan, Sitaxentan)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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