dicloxacillin
Trade name: pathocil
Approved
Apr 22, 1968
Dicloxacillin sodium USP is a semisynthetic antibiotic substance which resists destruction by the enzyme penicillinase (beta-lactamase). It is monosodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-4- isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]heptane-2-carboxylate monohydrate. Like other β-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. Dicloxacillin is administered orally via capsule form or powder for reconstitution. — NCATS
Clinical trial activity
8 trials · 10 clinical orgs · 8 marketing orgs
Earliest trial started Apr 1, 2002 (NCT00037050)
Timeline
1960s
- Apr 22, 1968
Wyeth — Earliest FDA Approval
- Apr 22, 1968
American Home Products — NDA Secondary Org
- Apr 22, 1968
Wyeth — NDA Organization
1970s
- Apr 1, 1971
Apothecon — Marketing Organization
- Apr 1, 1971
Sandoz — Marketing Organization
- Apr 1, 1971
Chartwell Pharmaceuticals — Marketing Organization
- Dec 31, 1979
GlaxoSmithKline — Marketing Organization
1980s
- Jun 3, 1982
Teva — Marketing Organization
2000s
- Jan 1, 2002
Earliest Phase 3 Sponsor(trial)
2010s
- Jan 1, 2016
Earliest Phase 1 Sponsor(trial)
2020s
- Sep 23, 2022
Aurobindo Pharma — Marketing Organization
Indications
Approved for
Studied for
- Arthritis, Infectious · Phase 4
- Bacteremia · Phase 4
- Bacterial Infections · Phase 3
- Bone Diseases, Infectious · Phase 4
- Dermatitis, Atopic · Phase 4
- Drug Interactions · Phase 1
- Eczema · Phase 4
- Endocarditis · Phase 4
- Gram-Positive Bacterial Infections · Phase 3
- Healthy Volunteers · Phase 1
- Infections · Phase 4
- Osteomyelitis · Phase 4
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
- approvedApr 22, 1968
Chemistry & pharmacology
SMILES
Cc1onc(-c2c(Cl)cccc2Cl)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O- Mol. weight
- 470.33 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
- ChEMBLCHEMBL893 ↗
- WikipediaDicloxacillin ↗
- NCATSCOF19H7WBK ↗
- ChEMBLCHEMBL1200701 ↗
Also known as
- (2s,5r,6r)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- (2s,5r,6r)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- brl-1702
- brl-1702
- dicloxacilina
- dicloxacilina
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillin
- dicloxacillina
- dicloxacillina
- dicloxacilline
- dicloxacilline
- dicloxacillin sodium
- dicloxacillin sodium
- dicloxacillin sodium
- dicloxacillin sodium
- dicloxacillin sodium hydrate
- dicloxacillinum
- dicloxacillinum
- dicloxacycline
- dycill
- dycill
- dynapen
- dynapen
- p-1011
- p-1011
- pathocil
- pathocil
- pathocil
- r-13423
- r-13423
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05578482 | Phase 4 | Oct 24, 2022 | Novo Nordisk, University Hospital Bispebjerg and Frederiksberg, University of Copenhagen |
| NCT05398679 | Phase 4 | Jun 1, 2022 | University of Barcelona |
| NCT05156437 | Phase 4 | Dec 20, 2021 | West Virginia University |
| NCT05073627 | Phase 1 | Nov 1, 2021 | University of Southern Denmark |
| NCT04563325 | Phase 4 | Sep 15, 2020 | Copenhagen Health Science Partners, Innovation Fund Denmark, University of Copenhagen |
| NCT03108690 | Phase 4 | May 1, 2017 | University of Copenhagen |
| NCT02983890 | Phase 1 | Sep 1, 2016 | Odense University Hospital, University of Southern Denmark |
| NCT00037050 | Phase 3 | Apr 1, 2002 | Pfizer |
Organizations
Research & Development (10)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| University of Copenhagen | Academic/Hospital | 3 | 3 | 1 | 2017 |
| University of Southern Denmark | Academic/Hospital | 2 | 1 | 1 | 2016 |
| Copenhagen Health Science Partners | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Innovation Fund Denmark | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Novo Nordisk | For profit | 1 | 0 | 1 | 2022 |
| Odense University Hospital | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Pfizer | For profit | 1 | 1 | 1 | 2002 |
| University Hospital Bispebjerg and Frederiksberg | Academic/Hospital | 1 | 0 | 1 | 2022 |
| University of Barcelona | Academic/Hospital | 1 | 1 | 1 | 2022 |
| West Virginia University | Academic/Hospital | 1 | 1 | 1 | 2021 |
Marketing (9)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| American Home Products | For profit | NDA2 | Apr 22, 1968 |
| Apothecon | For profit | MKTG | Apr 1, 1971 |
| Apothecon | For profit | NDA2 | — |
| Aurobindo Pharma | For profit | MKTG | Sep 23, 2022 |
| Chartwell Pharmaceuticals | For profit | MKTG | Apr 1, 1971 |
| GlaxoSmithKline | For profit | MKTG | Dec 31, 1979 |
| Sandoz | For profit | MKTG | Apr 1, 1971 |
| Teva | For profit | MKTG | Jun 3, 1982 |
| Wyeth | For profit | NDA | Apr 22, 1968 |