Diphenoxylate

Diphenoxylate
Clinical data


AHFS/Drugs.com	Monograph
Routes of administration	Oral
ATC code	A07DA01 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage II (Prohibited) UK: Class A US: Schedule II (alone) and V (with atropine)
Pharmacokinetic data
Protein binding	74-95%
Biological half-life	12–14 hours
Identifiers
IUPAC name ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
Synonyms	R-1132, NIH-756
CAS Number	915-30-0^Y
PubChem CID	13505
IUPHAR/BPS	7164
DrugBank	DB01081^Y
ChemSpider	12919^Y
UNII	73312P173G
KEGG	D07861^Y
ChEBI	CHEBI:4639^Y
ChEMBL	CHEMBL1201294^N
ECHA InfoCard	100.011.837
Chemical and physical data
Formula	C₃₀H₃₂N₂O₂
Molar mass	452.587 g/mol
3D model (Jmol)	Interactive image
SMILES N#CC(c1ccccc1)(c2ccccc2)CCN4CCC(c3ccccc3)(C(=O)OCC)CC4
InChI InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3^Y Key:HYPPXZBJBPSRLK-UHFFFAOYSA-N^Y
^NY (what is this?)

Diphenoxylate (INN, BAN) (brand name Diocalm), or diphenoxylate hydrochloride (USAN), is a centrally active opioid drug of the phenylpiperidine series that is used for the treatment of diarrhea. It acts by slowing intestinal contractions and peristalsis allowing the body to consolidate intestinal contents and prolong transit time, thus allowing the intestines to draw moisture out of them at a normal or higher rate and therefore stop the formation of loose and liquid stools. It is the main active ingredient in the anti-peristaltic medication Lomotil, which also contains atropine.

Diphenoxylate is the prototype of a small subfamily of opioids (the phenylpiperidines) including difenoxin (diphenoxylic acid), an active metabolite of diphenoxylate produced in the human body, and loperamide, which unlike the former two works exclusively in the intestines because it only crosses the blood–brain barrier in very small amounts. It was discovered at Janssen Pharmaceutica in 1956. It is a congener to the narcotic pethidine. Other somewhat more distant relatives include alphaprodine and piritramide.

Diphenoxylate works by decreasing the speed and amplitude of wave-like movements of the intestines (peristalsis) therefore allowing the body time to remove moisture from the intestinal contents and consolidate waste product into a dense solid form rather than loose and watery as is diarrhea.

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Wikipedia