nafcillin
Trade name: unipen
Approved
Oct 11, 1965
Nafcillin is a beta-lactam antibiotic of penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins. — NCATS
Clinical trial activity
7 trials · 8 clinical orgs · 17 marketing orgs
Earliest trial started Aug 1, 2003 (NCT00062647)
Timeline
1960s
- Oct 11, 1965
Wyeth — Earliest FDA Approval
- Oct 11, 1965
American Home Products — NDA Secondary Org
- Oct 11, 1965
Wyeth — NDA Organization
1980s
- Aug 2, 1984
Sandoz — Marketing Organization
- Dec 19, 1986
GlaxoSmithKline — Marketing Organization
- Sep 29, 1988
Watson Pharmaceuticals — Marketing Organization
- Oct 31, 1989
Baxalta — NDA Secondary Org
- Oct 31, 1989
Baxter — NDA Secondary Org
2000s
- Jan 1, 2003
Earliest Phase 2 Sponsor(trial)
2010s
- Apr 20, 2011
Istituto Bio Ita Spa — Marketing Organization
- Oct 3, 2011
Antibiotice — Marketing Organization
- Aug 24, 2012
Sagent Pharmaceuticals, Inc. — Marketing Organization
- Dec 26, 2012
Aurobindo Pharma — Marketing Organization
- Dec 26, 2012
Eugia Pharma — Marketing Organization
- Jan 1, 2013
Earliest Phase 3 Sponsor(trial)
- Apr 7, 2014
Mylan — Marketing Organization
- Apr 7, 2014
STERISCIENCE — Marketing Organization
- Apr 7, 2014
ONESOURCE SPECIALTY — Marketing Organization
- Dec 10, 2019
Fresenius — Marketing Organization
2020s
- Jan 1, 2021
Earliest Phase 1 Sponsor(trial)
Indications
Approved for
Studied for
- Cerebral Hemorrhage · Phase 1
- Cerebral Ventriculitis · Phase 1
- Dermatology · Phase 4
- Gram-Positive Bacterial Infections · Phase 2
- Hydrocephalus · Phase 1
- Kidney Failure, Chronic · Phase 4
- Osteomyelitis · Phase 3
- Staphylococcal Infections · Phase 2
- Staphylococcus aureus · Phase 4
- Subarachnoid Hemorrhage · Phase 1
Mechanism of action
- Penicillin-binding proteinINHIBITOR
Penicillin-binding protein inhibitor
- Penicillin-binding protein 4 (pbp4) ↗
- Cell division protein FtsI [Peptidoglycan synthetase] / Transpeptidase, Penicillin binding protein transpeptidase domain, Penicillin-binding protein 3 (pbpF) ↗
- MecA PBP2' (penicillin binding protein 2') (Q53707) ↗
- Penicillin-binding protein 2 (Q53729) ↗
- Cell division protein FtsI (Peptidoglycan synthetase) (pbpA) ↗
Approval history
- approvedOct 11, 1965
Chemistry & pharmacology
SMILES
CCOc1ccc2ccccc2c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)[O-].O.[Na+]- Mol. weight
- 454.48 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1568276 ↗
- WikipediaNafcillin ↗
- NCATS4CNZ27M7RV ↗
- ChEMBLCHEMBL1443 ↗
- ChEMBLCHEMBL1200344 ↗
Also known as
- (2-ethoxy-1-naphthalenyl)penicillin
- (2-ethoxy-1-naphthalenyl)penicillin
- (2-ethoxy-1-naphthyl)penicillin
- (2-ethoxy-1-naphthyl)penicillin
- (2s,5r,6r)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- (2s,5r,6r)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 6-(2-ethoxy-1-naphthamido)penicillanic acid
- 6-(2-ethoxy-1-naphthamido)penicillanic acid
- nafcilin
- nafcilina
- nafcilina
- nafcillin
- nafcillin
- nafcillin
- nafcillin
- nafcillin
- nafcillin
- nafcillin
- nafcillin
- nafcilline
- nafcilline
- nafcillin sodium
- nafcillin sodium
- nafcillin sodium
- nafcillin sodium
- nafcillin sodium salt
- nafcillin sodium salt monohydrate
- nafcillinum
- nafcillinum
- nallpen
- nallpen
- nallpen
- naphcillin
- naphcillin
- naphcillin
- naphthamidopenicillin
- naphthamidopenicillin
- naphthamidopenicillin
- naphthamidopenicillin
- naphthamidopenicillin
- naphthamidopenicillin
- unipen
- unipen
- unipen
- wy-3277
- wy-3277
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05001750 | Phase 1 | Jun 14, 2021 | Yeshiva University |
| NCT04775953 | Phase 2 | Apr 22, 2021 | National Institute of Allergy and Infectious Diseases (NIAID) |
| NCT02344511 | Phase 3 | Mar 1, 2016 | Actavis, Allergan |
| NCT01922011 | Phase 3 | Sep 1, 2013 | Cubist, Merck |
| NCT01104662 | Phase 4 | Apr 1, 2010 | Cubist |
| NCT00428844 | Phase 2 | Jan 1, 2007 | Cubist |
| NCT00062647 | Phase 2 | Aug 1, 2003 | Duke University, Theravance |
Organizations
Research & Development (8)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Cubist | For profit | 3 | 3 | 3 | 2007 |
| Actavis | For profit | 1 | 1 | 1 | 2016 |
| Allergan | For profit | 1 | 0 | 1 | 2016 |
| Duke University | Academic/Hospital | 1 | 0 | 1 | 2003 |
| Merck | For profit | 1 | 0 | 1 | 2013 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 1 | 1 | 1 | 2021 |
| Theravance | For profit | 1 | 1 | 1 | 2003 |
| Yeshiva University | Academic/Hospital | 1 | 1 | 1 | 2021 |
Marketing (19)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| American Home Products | For profit | NDA2 | Oct 11, 1965 |
| American Home Products | For profit | MKTG | — |
| Antibiotice | For profit | MKTG | Oct 3, 2011 |
| Apothecon | For profit | MKTG | — |
| Aurobindo Pharma | For profit | MKTG | Dec 26, 2012 |
| Baxalta | For profit | NDA2 | Oct 31, 1989 |
| Baxter | For profit | NDA2 | Oct 31, 1989 |
| Eugia Pharma | For profit | MKTG | Dec 26, 2012 |
| Fresenius | For profit | MKTG | Dec 10, 2019 |
| GlaxoSmithKline | For profit | MKTG | Dec 19, 1986 |
| Istituto Bio Ita Spa | For profit | MKTG | Apr 20, 2011 |
| Mylan | For profit | MKTG | Apr 7, 2014 |
| ONESOURCE SPECIALTY | For profit | MKTG | Apr 7, 2014 |
| STERISCIENCE | For profit | MKTG | Apr 7, 2014 |
| STERISCIENCE | For profit | SYN | Apr 7, 2014 |
| Sagent Pharmaceuticals, Inc. | For profit | MKTG | Aug 24, 2012 |
| Sandoz | For profit | MKTG | Aug 2, 1984 |
| Watson Pharmaceuticals | For profit | MKTG | Sep 29, 1988 |
| Wyeth | For profit | NDA | Oct 11, 1965 |