Chemistry:Olopatadine

Short description: Chemical compound

Olopatadine

Clinical data
Trade names	Patanol, Pataday, Opatanol
AHFS/Drugs.com	Monograph
MedlinePlus	a602025
License data	US DailyMed: Olopatadine
Pregnancy category	AU: B1
Routes of administration	Eye drops, nasal spray
ATC code	S01GX09 (WHO) R01AC08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only / OTC EU: Rx-only
Pharmacokinetic data
Elimination half-life	3 hours
Identifiers
IUPAC name {(11Z)-11-[3-(dimethylamino)propylidene]-6,11- dihydrodibenzo[b,e]oxepin-2-yl}acetic acid
CAS Number	113806-05-6 Y
PubChem CID	5281071
DrugBank	DB00768 Y
ChemSpider	4444528 Y
UNII	D27V6190PM
KEGG	D08293 Y as HCl: D01192 Y
ChEMBL	ChEMBL1189432 N
Chemical and physical data
Formula	C21H23NO3
Molar mass	337.419 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(O)Cc2ccc1OCc3c(C(\c1c2)=C\CCN(C)C)cccc3
InChI InChI=1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8- Y Key:JBIMVDZLSHOPLA-LSCVHKIXSA-N Y
NY (what is this?)  (verify)

Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis (hay fever). It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

Common side effects include headache, sore throat, eye discomfort, or changes in perception of taste. More significant side effects may include sleepiness. It is unclear if use during pregnancy or breastfeeding is safe. It is an antihistamine and mast cell stabilizer.

Olopatadine was patented in 1986 and came into medical use in 1997. It is available as a generic medication. In 2021, it was the 263rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.

Side effects

Some known side effects include headache (7% of occurrence), eye burning and/or stinging (5%), blurred vision, dry eyes, foreign body sensation, hyperemia, keratitis, eyelid edema, pruritus, asthenia, sore throat (pharyngitis), rhinitis, sinusitis, taste perversion, and vomiting.

Chemistry

Synthesis

Olopatadine synthesis:

Pharmacology

Pharmacodynamics

Olopatadine acts as a selective antagonist of the histamine H₁ receptor, thus stabilizing mast cells and inhibiting histamine release.

History

Olopatadine was patented in 1986 by Kyowa Hakko Kogyo and came into medical use in 1997.

In the United States, Pataday Twice Daily Relief was first approved by the FDA in 1996, under the name Patanol as a prescription drug and was indicated for the treatment of the signs and symptoms of allergic conjunctivitis (referring to ocular redness and itching due to allergies). Pataday – now Pataday Once Daily Relief – was first approved by the FDA in 2004, as a prescription drug and was indicated for the treatment of ocular itching associated with allergic conjunctivitis. These drugs are mast cell stabilizers, which work by preventing the release of histamine and therefore prevent or control allergic disorders.

In February 2020, Pataday Twice Daily Relief and Pataday Once Daily Relief were switched to be over-the-counter drugs in the United States when the FDA granted the approvals of the nonprescription products to Alcon.

Society and culture

Brand names

Brand names include Pazeo, Pataday, Patanol S, Patanol, Opatanol, Olopat, Patanase. It is also available as an oral tablet in Japan under the tradename Allelock, manufactured by Kyowa Hakko Kogyo.

External links

• "Olopatadine Nasal Spray". https://medlineplus.gov/druginfo/meds/a615038.html.