propoxyphene
Trade name: Darvon
Approved
Aug 16, 1957
Propoxyphene is a centrally acting opiate analgesic. Propoxyphene is an odorless, freely soluble in water, white crystalline powder with a bitter taste. In vitro studies demonstrated propoxyphene and the metabolite norpropoxyphene inhibit sodium channels (local anesthetic effect) with norpropoxyphene being approximately 2 fold more potent than propoxyphene and propoxyphene approximately 10 fold more potent than lidocaine. Propoxyphene and norpropoxyphene inhibit the voltage-gated potassium current carried by cardiac rapidly activating delayed rectifier (hERG) channels with approximately equal potency. It is unclear if the effects on ion channels occur within therapeutic dose range. Propoxyphene is indicated for the relief of mild to moderate pain. — NCATS
Clinical trial activity
3 trials · 4 clinical orgs · 32 marketing orgs
Earliest trial started Mar 1, 2008 (NCT00652093)
Timeline
1950s
- Aug 16, 1957
Earliest FDA Approval
- Aug 16, 1957
Xanodyne Pharmaceuticals — NDA Secondary Org
1970s
- Dec 22, 1970
Sandoz — Marketing Organization
- Sep 9, 1971
Xanodyne Pharmaceuticals — First NDA Organization
- Sep 9, 1971
AAIPharma — NDA Secondary Org
- Sep 9, 1971
Xanodyne Pharmaceuticals — NDA Organization
- Nov 30, 1971
Par Pharmaceuticals — Marketing Organization
- Aug 7, 1972
Watson Pharmaceuticals — Marketing Organization
- Sep 15, 1972
Heritage Pharma — Marketing Organization
- Nov 2, 1972
Nexgen Pharma, Inc — Marketing Organization
- Dec 18, 1972
Mutual Pharmaceutical — Marketing Organization
- Jan 15, 1973
Puracap Pharmaceutical — Marketing Organization
- Jun 6, 1973
MK Labs — Marketing Organization
- Jun 20, 1973
West-Ward Pharmaceutical — Marketing Organization
- Aug 13, 1973
Roxane Laboratories — Marketing Organization
- Oct 23, 1973
Impax Laboratories — Marketing Organization
- Sep 23, 1975
Alta Pharma — Marketing Organization
- Aug 20, 1976
Mylan — Marketing Organization
- Sep 3, 1976
Caraco Pharmaceutical Laboratories — Marketing Organization
1980s
- Oct 22, 1984
Teva — Marketing Organization
- Jan 2, 1987
Actavis — Marketing Organization
- Jan 6, 1987
Superpharm — Marketing Organization
- May 13, 1988
Halsey — Marketing Organization
1990s
- Feb 12, 1997
Vintage — Marketing Organization
2000s
- Feb 2, 2001
Mallinckrodt — Marketing Organization
- Feb 2, 2001
International Minerals and Chemical Corporation — Marketing Organization
- Jul 11, 2001
Able Laboratories — Marketing Organization
- Sep 10, 2003
Xanodyne Pharmaceuticals — Marketing Organization
- May 7, 2004
Rafael Pharmaceuticals Inc. — Marketing Organization
- Mar 16, 2007
Wockhardt — Marketing Organization
- Jan 1, 2008
Xanodyne Pharmaceuticals — Earliest Phase 3 Sponsor(trial)
- Feb 11, 2008
Mirror Pharms — Marketing Organization
- Jul 17, 2009
Apax Partners — Marketing Organization
Indications
Approved for
Mechanism of action
- Mu opioid receptorAGONIST
OPRM agonist
Combination products
darvocet
with acetaminophen
Also known as darvocet a, darvocet-n, wygesic
darvon compoun
with caffeine, acetylsalicylic acid
Also known as compoun, propoxyphene compoun
darvon w/ asa
with acetylsalicylic acid
Also known as darvon-n w/ asa
Approval history
- approvedPriority reviewAug 16, 1957
Chemistry & pharmacology
SMILES
O.OS(=O)(=O)C1=CC=C2C=CC=CC2=C1.CCC(=O)O[C@@](CC3=CC=CC=C3)([C@H](C)CN(C)C)C4=CC=CC=C4- Mol. weight
- 565.72 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaDextropropoxyphene ↗
- NCATS38M219L1OJ ↗
- ChEMBLCHEMBL3989716 ↗
- ChEMBLCHEMBL1237104 ↗
- ChEMBLCHEMBL1213351 ↗
Also known as
- 2-naphthalenesulfonic acid, compd. with (s-(r*,s*))-3-(dimethylamino)-2-methyl-1-phenyl-1-(phenylmethyl)p- ropyl propanoate (1:1)
- darvon
- darvon
- darvon
- darvon-n
- darvon-n
- dextropropoxyphene
- dolene
- dolene
- doloxene
- doloxene
- kesso-gesic
- kesso-gesic
- levopropoxyphene napsylate
- levopropoxyphene napsylate anhydrous
- levopropoxyphene napsylate, anhydrous
- prophene 65
- prophene 65
- propoxyphene
- propoxyphene
- propoxyphene
- propoxyphene
- propoxyphene
- propoxyphene hcl
- propoxyphene hcl
- propoxyphene hcl
- propoxyphene hydrochloride
- propoxyphene hydrochloride
- propoxyphene hydrochloride
- propoxyphene hydrochloride
- propoxyphene hydrochloride 65
- propoxyphene hydrochloride 65
- propoxyphene napsylate
- propoxyphene napsylate
- propoxyphene napsylate
- propoxyphene napsylate
- propoxyphene napsylate
- propoxyphene napsylate
- propoxyphene napsylate
- propoxyphene napsylate
- xp20b
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01133873 | Phase 4 | Jun 1, 2010 | Lifetree Clinical Research, Xanodyne Pharmaceuticals |
| NCT00655291 | Phase 3 | Apr 1, 2008 | Xanodyne Pharmaceuticals |
| NCT00652093 | Phase 4 | Mar 1, 2008 | Endo Pharmaceuticals, University of Rochester |
Organizations
Research & Development (4)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Xanodyne Pharmaceuticals | For profit | 2 | 2 | 2 | 2008 |
| Endo Pharmaceuticals | For profit | 1 | 0 | 1 | 2008 |
| Lifetree Clinical Research | For profit | 1 | 0 | 1 | 2010 |
| University of Rochester | Academic/Hospital | 1 | 1 | 1 | 2008 |
Marketing (38)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| AAIPharma | For profit | NDA2 | Sep 9, 1971 |
| Able Laboratories | For profit | MKTG | Jul 11, 2001 |
| Actavis | For profit | MKTG | Jan 2, 1987 |
| Alta Pharma | For profit | MKTG | Sep 23, 1975 |
| Apax Partners | For profit | MKTG | Jul 17, 2009 |
| Bausch Health Companies | For profit | MKTG | — |
| Caraco Pharmaceutical Laboratories | For profit | MKTG | Sep 3, 1976 |
| Halsey | For profit | MKTG | May 13, 1988 |
| Heritage Pharma | For profit | MKTG | Sep 15, 1972 |
| Impax Laboratories | For profit | MKTG | Oct 23, 1973 |
| International Minerals and Chemical Corporation | For profit | MKTG | Feb 2, 2001 |
| Lederle | For profit | MKTG | — |
| MK Labs | For profit | MKTG | Jun 6, 1973 |
| Mallinckrodt | For profit | MKTG | Feb 2, 2001 |
| Mirror Pharms | For profit | MKTG | Feb 11, 2008 |
| Mutual Pharmaceutical | For profit | MKTG | Dec 18, 1972 |
| Mylan | For profit | SYN | Oct 25, 1974 |
| Mylan | For profit | SYN | Dec 30, 1985 |
| Mylan | For profit | MKTG | Aug 20, 1976 |
| Nexgen Pharma, Inc | For profit | MKTG | Nov 2, 1972 |
| Par Pharmaceuticals | For profit | MKTG | Nov 30, 1971 |
| Puracap Pharmaceutical | For profit | MKTG | Jan 15, 1973 |
| Rafael Pharmaceuticals Inc. | For profit | MKTG | May 7, 2004 |
| Roxane Laboratories | For profit | MKTG | Aug 13, 1973 |
| Sandoz | For profit | MKTG | Dec 22, 1970 |
| Superpharm | For profit | MKTG | Jan 6, 1987 |
| Teva | For profit | SYN | Apr 14, 1978 |
| Teva | For profit | MKTG | Oct 22, 1984 |
| Vintage | For profit | MKTG | Feb 12, 1997 |
| Warner Chilcott | For profit | MKTG | — |
| Watson Pharmaceuticals | For profit | MKTG | Aug 7, 1972 |
| Watson Pharmaceuticals | For profit | SYN | Nov 16, 2004 |
| West-Ward Pharmaceutical | For profit | MKTG | Jun 20, 1973 |
| Whiteworth Towne Paulsen | For profit | MKTG | — |
| Wockhardt | For profit | MKTG | Mar 16, 2007 |
| Xanodyne Pharmaceuticals | For profit | NDA2 | Aug 16, 1957 |
| Xanodyne Pharmaceuticals | For profit | NDA | Sep 9, 1971 |
| Xanodyne Pharmaceuticals | For profit | MKTG | Sep 10, 2003 |