User:Mr. Ibrahem/Dextropropoxyphene

Mr. Ibrahem/Dextropropoxyphene
Clinical data
Trade names	Darvon, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682325
License data	US FDA: Propoxyphene;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
Legal status
Legal status	AU: S4 (Prescription only); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class C; US: Schedule II and Schedule IV (when in dosage form);
Pharmacokinetic data
Bioavailability	40%
Protein binding	78%
Metabolism	Liver-mediated, CYP3A4-mediated N-demethylation (major), aromatic hydroxylation (minor) and ester hydrolysis (minor)
Onset of action	< 1 hr
Elimination half-life	6–12 hours; 30–36 hours (active metabolite, nordextropropoxyphene)
Duration of action	Up to 6 hrs
Excretion	Urine (major), breastmilk (minor)
Identifiers
	IUPAC name (1S,2R)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propionate;
Chemical and physical data
Formula	C22H29NO2
Molar mass	339.479 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	75 °C (167 °F)
	SMILES CCC(=O)O[C@](Cc1ccccc1)(c2ccccc2)[C@H](C)CN(C)C;
	InChI InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1 ; Key:XLMALTXPSGQGBX-GCJKJVERSA-N ;
	(what is this?) (verify)

Dextropropoxyphene, which has been sold under the brand name Darvon among others, is a pain medication in the opioid category.^[2] It has been used for pain but the benefits are similar to paracetamol (acetaminophine) and less than ibuprofen.^[2]^[4] An equivalent amount has half the strength of codeine.^[5] It is taken by mouth.^[6] Onset of effects are within an hour and may last for up to 6 hours.^[2]

Side effects may include heart arrhythmias, decreased breathing, and seizures.^[7]^[2] It has a high risk of misuse and historically was a common cause of death from drug misuse.^[2]^[8] Some effects may be reversed with naloxone.^[9] Use during pregnancy may harm the baby.^[2]

Dextropropoxyphene came into medical use in the United States in 1957.^[2] It has subsequently been removed from the market in the United States, Canada, New Zealand, and India.^[7] While still available in Australia, there are restrictions as of 2014.^[7] In the United Kingdom it is not avaliable to new patients.^[9] It was generally sold as a combination medication with either paracetamol or aspirin.^[2]

References[edit]

^ ^a ^b ^c ^d Davis, MP; Glare, PA; Hardy, J (2009) [2005]. Opioids in Cancer Pain (2nd ed.). Oxford, UK: Oxford University Press. ISBN 978-0-19-157532-7.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Barkin, RL; Barkin, SJ; Barkin, DS (November 2006). "Propoxyphene (dextropropoxyphene): a critical review of a weak opioid analgesic that should remain in antiquity". American journal of therapeutics. 13 (6): 534–42. doi:10.1097/01.mjt.0000253850.86480.fb. PMID 17122535.
^ "PRODUCT INFORMATION PARADEX" (PDF). TGA eBusiness Services. Aspen Pharmacare Australia Pty Ltd. 2 March 2010. Archived from the original on 9 January 2016. Retrieved 9 April 2014.
^ Collins, SL; Edwards, JE; Moore, RA; McQuay, HJ (2000). "Single dose dextropropoxyphene, alone and with paracetamol (acetaminophen), for postoperative pain". The Cochrane database of systematic reviews (2): CD001440. doi:10.1002/14651858.CD001440. PMID 10796793.
^ Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 123. ISBN 978-0-470-01552-0. Archived from the original on 2021-08-28. Retrieved 2020-11-10.
^ Stannard, Cathy; Coupe, Michael; Pickering, Tony (2013). Opioids in Non-Cancer Pain. OUP Oxford. p. 34. ISBN 978-0-19-967807-5. Archived from the original on 2021-08-28. Retrieved 2020-11-10.
^ ^a ^b ^c Administration, Australian Government Department of Health Therapeutic Goods (7 January 2014). "Dextropropoxyphene: questions and answers". Therapeutic Goods Administration (TGA). Archived from the original on 13 October 2020. Retrieved 10 November 2020.
^ Drugs of Abuse, 2005 Edition, *. United States. Drug Enforcement Administration. p. 24. Archived from the original on 2021-08-28. Retrieved 2020-11-10.
^ ^a ^b BNF 79. London: Pharmaceutical Press. March 2020. p. 455, 1401. ISBN 978-0857113658.

[cancer-1] Davis, MP; Glare, PA; Hardy, J (2009) [2005]. Opioids in Cancer Pain (2nd ed.). Oxford, UK: Oxford University Press. ISBN 978-0-19-157532-7.

[Rob2006-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Barkin, RL; Barkin, SJ; Barkin, DS (November 2006). "Propoxyphene (dextropropoxyphene): a critical review of a weak opioid analgesic that should remain in antiquity". American journal of therapeutics. 13 (6): 534–42. doi:10.1097/01.mjt.0000253850.86480.fb. PMID 17122535.

[TGA-3] "PRODUCT INFORMATION PARADEX" (PDF). TGA eBusiness Services. Aspen Pharmacare Australia Pty Ltd. 2 March 2010. Archived from the original on 9 January 2016. Retrieved 9 April 2014.

[Col2000-4] Collins, SL; Edwards, JE; Moore, RA; McQuay, HJ (2000). "Single dose dextropropoxyphene, alone and with paracetamol (acetaminophen), for postoperative pain". The Cochrane database of systematic reviews (2): CD001440. doi:10.1002/14651858.CD001440. PMID 10796793.

[5] Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 123. ISBN 978-0-470-01552-0. Archived from the original on 2021-08-28. Retrieved 2020-11-10.

[6] Stannard, Cathy; Coupe, Michael; Pickering, Tony (2013). Opioids in Non-Cancer Pain. OUP Oxford. p. 34. ISBN 978-0-19-967807-5. Archived from the original on 2021-08-28. Retrieved 2020-11-10.

[TGA2014-7] Administration, Australian Government Department of Health Therapeutic Goods (7 January 2014). "Dextropropoxyphene: questions and answers". Therapeutic Goods Administration (TGA). Archived from the original on 13 October 2020. Retrieved 10 November 2020.

[DEA2005-8] Drugs of Abuse, 2005 Edition, *. United States. Drug Enforcement Administration. p. 24. Archived from the original on 2021-08-28. Retrieved 2020-11-10.

[BNF79-9] BNF 79. London: Pharmaceutical Press. March 2020. p. 455, 1401. ISBN 978-0857113658.

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