Tripelennamine

Tripelennamine

Systematic (IUPAC) name
N,N-dimethyl-N-(phenylmethyl)-N-pyridin-2-ylethane-1,2-diamine
Clinical data
AHFS/Drugs.com	Multum Consumer Information
MedlinePlus	a601044
Routes of administration	Oral, Intravenous
Legal status	℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic hydroxylation and glucuronidation
Biological half-life	4-6 hours[1]
Excretion	Renal
Identifiers
CAS Number	91-81-6 154-69-8 (monohydrochloride) 22306-05-4 (hydrochloride) 57116-36-6 (maleate) 6138-56-3 (citrate)
ATC code	D04AA04 (WHO) R06AC04
PubChem	CID 5587
IUPHAR/BPS	7318
DrugBank	DB00792
ChemSpider	5385
UNII	3C5ORO99TY
KEGG	D08645
ChEMBL	CHEMBL1241
Chemical data
Formula	C16H21N3
Molar mass	255.358 g/mol
SMILES CN(C)CCN(CC1=CC=CC=C1)C2=NC=CC=C2
InChI InChI=1S/C16H21N3/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3 Key:UFLGIAIHIAPJJC-UHFFFAOYSA-N
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Tripelennamine (sold as Pyribenzamine by Novartis) is a drug that is used as an antipruritic and first-generation antihistamine. It can be used in the treatment of asthma, hay fever, rhinitis and urticaria, but is now less common as it has been replaced by newer antihistamines.

Medical uses

Where and when it is/was in common use, tripelennamine is used much like other mildly-anticholinergic antihistamines for treating conditions of the upper respiratory tract arising from illnesses and hay fever. It can be used alone or in combination with other agents to have the desired effect. Cough medicine of the general formula tripelennamine + codeine/dihydrocodine/hydrocodone ± expectorant ± decongestant(s) is quite popular where available. One example is the line of Pyribenzamine Cough Syrups which contains codeine and with and without decongestants listed in the 1978 Physicians' Desk Reference; the codeine-tripelennamine synergy is well-known and does make such mixtures more useful for their intended purposes.

Side effects

Tripelennamine is mildly sedating. Other side effects can include irritation, dry mouth, nausea, and dizziness.

Pharmacology

Tripelennamine acts primarily as an antihistamine, or H₁ receptor antagonist. It has little to no anticholinergic activity. In addition to its antihistamine properties, tripelennamine also acts as a weak serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).^[2][3][4] Because of its SRI properties, tripelennamine was used as the basis for the development of the selective serotonin reuptake inhibitor (SSRI) fluvoxamine (Luvox).^[5]

History

Tripelennamine was first synthesized in 1946 by Carl Djerassi, working in the laboratory of Charles Huttrer at Ciba, shortly after Djerassi got his B.S. It was his first patent.

See also

• Chloropyramine
• Mepyramine
• Pheniramine

References

1. Lewis R. Goldfrank; Neal Flomenbaum (2006). Goldfrank's toxicologic emergencies. McGraw-Hill Professional. p. 787. ISBN 978-0-07-147914-1. Retrieved 27 November 2011.
2. Oishi R, Shishido S, Yamori M, Saeki K (February 1994). "Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain". Naunyn-Schmiedeberg's Archives of Pharmacology 349 (2): 140–4. doi:10.1007/bf00169830. PMID 7513381.
3. Sato T, Suemaru K, Matsunaga K, Hamaoka S, Gomita Y, Oishi R (May 1996). "Potentiation of L-dopa-induced behavioral excitement by histamine H1-receptor antagonists in mice". Japanese Journal of Pharmacology 71 (1): 81–4. doi:10.1254/jjp.71.81. PMID 8791174.
4. Yeh SY, Dersch C, Rothman R, Cadet JL (September 1999). "Effects of antihistamines on 3, 4-methylenedioxymethamphetamine-induced depletion of serotonin in rats". Synapse 33 (3): 207–17. doi:10.1002/(SICI)1098-2396(19990901)33:3<207::AID-SYN5>3.0.CO;2-8. PMID 10420168.
5. ), David Healy (MRC Psych (January 2004). Let them eat Prozac: the unhealthy ... - Google Books. ISBN 978-0-8147-3669-2.