phenoxymethylpenicillin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, 6-aminopenicillanic acid derivatives	2083	87-08-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: penicillin v penicillin v potassium phenopenicillin meropenin phenoxymethylpenicillin phenoxymethylpenicillinic acid	A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms. Molecular weight: 350.39 Formula: C16H18N2O5S CLOGP: 1.94 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 95.94 ALOGS: -2.89 ROTB: 5

Molecule

Description

Molfile Inchi Smiles

Synonyms:

penicillin v
penicillin v potassium
phenopenicillin
meropenin
phenoxymethylpenicillin
phenoxymethylpenicillinic acid

A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.

Molecular weight: 350.39
Formula: C16H18N2O5S
CLOGP: 1.94
LIPINSKI: 0
HAC: 7
HDO: 2
TPSA: 95.94
ALOGS: -2.89
ROTB: 5

Drug dosage:

Dose	Unit	Route
2	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.25 mg/mL	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	71.35 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.41 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	6.80 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.45 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.84 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 13, 1958	FDA	WYETH AYERST

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug hypersensitivity	266.34	17.87	236	6030	243589	46436207
Rash	158.17	17.87	215	6051	356297	46323499
Myocardial depression	116.84	17.87	24	6242	484	46679312
Lip swelling	107.20	17.87	57	6209	25338	46654458
Decorticate posture	106.65	17.87	21	6245	339	46679457
Hypersensitivity	75.96	17.87	97	6169	150224	46529572
Swelling face	62.70	17.87	54	6212	53005	46626791
Ventricular hypokinesia	56.17	17.87	21	6245	4057	46675739
Urticaria	50.15	17.87	70	6196	117822	46561974
Lichen nitidus	44.92	17.87	8	6258	72	46679724
Hypothermia	44.86	17.87	25	6241	12158	46667638
Rash macular	43.75	17.87	29	6237	19231	46660565
Coma scale abnormal	38.62	17.87	17	6249	4989	46674807
Drug reaction with eosinophilia and systemic symptoms	36.77	17.87	31	6235	29517	46650279
Eosinophilia	36.70	17.87	26	6240	19191	46660605
Oral discomfort	34.02	17.87	18	6248	7900	46671896
Respiratory depression	27.64	17.87	18	6248	11582	46668214
Swollen tongue	27.13	17.87	26	6240	29206	46650590
Agranulocytosis	27.03	17.87	23	6243	22162	46657634
Pruritus	25.62	17.87	81	6185	242271	46437525
Acute respiratory distress syndrome	25.23	17.87	22	6244	21900	46657896
Intravascular haemolysis	24.44	17.87	6	6260	276	46679520
Encephalopathy	24.10	17.87	26	6240	33563	46646233
Hepatobiliary infection	24.03	17.87	4	6262	23	46679773
Unresponsive to stimuli	23.25	17.87	25	6241	32149	46647647
Intentional overdose	22.43	17.87	35	6231	64909	46614887
Lichenification	22.37	17.87	6	6260	393	46679403
Hepatocellular injury	21.44	17.87	23	6243	29499	46650297
Toxic epidermal necrolysis	21.02	17.87	20	6246	22258	46657538
Mouth swelling	20.56	17.87	10	6256	3679	46676117
Left ventricular dysfunction	19.86	17.87	14	6252	10241	46669555
Sickle cell anaemia with crisis	19.81	17.87	10	6256	3982	46675814
Vomiting projectile	18.69	17.87	7	6259	1358	46678438
Jaundice	18.40	17.87	21	6245	28824	46650972

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug hypersensitivity	102.96	16.94	93	5632	68426	29878327
Nocardiosis	81.42	16.94	29	5696	3426	29943327
Rash	68.14	16.94	127	5598	191762	29754991
Brief psychotic disorder with marked stressors	54.78	16.94	11	5714	135	29946618
Swelling face	51.20	16.94	38	5687	21166	29925587
Morganella infection	44.16	16.94	11	5714	374	29946379
Pleocytosis	41.94	16.94	11	5714	461	29946292
Acute generalised exanthematous pustulosis	40.92	16.94	21	5704	6077	29940676
Spinal muscular atrophy	40.47	16.94	9	5716	185	29946568
Bronchial haemorrhage	37.21	16.94	11	5714	718	29946035
Pyrexia	36.44	16.94	131	5594	294358	29652395
Respiratory tract infection bacterial	30.98	16.94	9	5716	552	29946201
Toxoplasmosis	29.36	16.94	10	5715	1033	29945720
Pneumococcal sepsis	29.16	16.94	9	5716	680	29946073
Thrombotic microangiopathy	29.15	16.94	19	5706	8591	29938162
Skin exfoliation	28.11	16.94	28	5697	23144	29923609
Prothrombin level abnormal	27.84	16.94	6	5719	106	29946647
Rash papular	26.66	16.94	18	5707	8627	29938126
Brain abscess	26.37	16.94	12	5713	2669	29944084
Skin swelling	26.35	16.94	9	5716	938	29945815
Sinusitis bacterial	26.31	16.94	7	5718	310	29946443
Drug reaction with eosinophilia and systemic symptoms	25.00	16.94	29	5696	28459	29918294
Death	23.94	16.94	20	5705	357263	29589490
Disease complication	23.58	16.94	11	5714	2588	29944165
Plasma cell myeloma	23.53	16.94	39	5686	53423	29893330
Antipsychotic drug level decreased	23.18	16.94	8	5717	860	29945893
Increased bronchial secretion	23.17	16.94	9	5716	1350	29945403
Swelling	22.61	16.94	31	5694	35944	29910809
Lip swelling	22.49	16.94	19	5706	12725	29934028
Parvovirus B19 infection	22.25	16.94	7	5718	563	29946190
Conjunctivitis bacterial	21.44	16.94	5	5720	128	29946625
Sputum increased	20.46	16.94	9	5716	1848	29944905
Tonsil cancer	20.20	16.94	7	5718	761	29945992
Mouth haemorrhage	19.29	16.94	12	5713	5005	29941748
Chest X-ray abnormal	17.65	16.94	10	5715	3517	29943236
Metabolic disorder	17.43	16.94	10	5715	3601	29943152
Sleep disorder due to general medical condition, insomnia type	17.13	16.94	7	5718	1199	29945554
Resuscitation	16.98	16.94	7	5718	1225	29945528
Inflammation	16.98	16.94	21	5704	22005	29924748

Pharmacologic Action:

Source	Code	Description
ATC	J01CE02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE BETA-LACTAM ANTIBACTERIALS, PENICILLINS Beta-lactamase sensitive penicillins
FDA CS	M0016152	Penicillins
FDA EPC	N0000175497	Penicillin-class Antibacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Acute otitis media	indication	3110003
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Gingivostomatitis	indication	20607006
Scarlet fever	indication	30242009	DOID:8596
Streptococcal tonsillitis	indication	41582007
Erysipelas	indication	44653001	DOID:11330
Upper respiratory infection	indication	54150009
Streptococcus pyogenes infection	indication	302809008
Infective otitis media	indication	312218008
Fusospirochetal pharyngitis	indication	399095008
Pharyngitis	indication	405737000	DOID:2275
Infection due to Staphylococcus aureus	indication	406602003
Pneumococcal Acute Otitis Media	indication
Upper Respiratory Pneumococcal Infection	indication
Infection Prevention from Tooth Extraction	indication
Rheumatic Fever Prevention	indication
Upper Respiratory Streptococcal Infection	indication
Actinomycotic infection	off-label use	11817007	DOID:8478
Lyme disease	off-label use	23502006	DOID:11729
Infection due to anaerobic bacteria	off-label use	423451008
Pneumococcal Infection Prevention in Sickle Cell Disease	off-label use
Kidney disease	contraindication	90708001	DOID:557
Infectious mononucleosis	contraindication	271558008	DOID:8568
Pseudomembranous enterocolitis	contraindication	397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.79	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Bacterial penicillin-binding protein	Enzyme		DACA_ECOLI DACB_ECOLI DACC_ECOLI FTSI_ECOLI PBP2_ECOLI PBPA_ECOLI PBPB_ECOLI	INHIBITOR				CHEMBL	CHEMBL
Penicillin-binding protein 1A	Enzyme		PBPA_CLOPE					WOMBAT-PK

External reference:

ID	Source
N0000011298	NUI
D05411	KEGG_DRUG
132-98-9	SECONDARY_CAS_RN
4017436	VANDF
C0030840	UMLSCUI
CHEBI:27446	CHEBI
PNV	PDB_CHEM_ID
CHEMBL615	ChEMBL_ID
CHEMBL1200852	ChEMBL_ID
D010404	MESH_DESCRIPTOR_UI
DB00417	DRUGBANK_ID
10920	IUPHAR_LIGAND_ID
518	INN_ID
Z61I075U2W	UNII
4731	PUBCHEM_CID
203195	RXNORM
179406	MMSL
2179	MMSL
5248	MMSL
d07730	MMSL
002684	NDDF
002686	NDDF
372725003	SNOMEDCT_US
39359008	SNOMEDCT_US
56723006	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0093-1172	TABLET	250 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0093-1174	TABLET	500 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0093-4125	POWDER, FOR SOLUTION	125 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0093-4127	POWDER, FOR SOLUTION	250 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9836	TABLET, FILM COATED	500 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9837	TABLET, FILM COATED	250 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0440-2055	TABLET	250 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0440-8055	TABLET	250 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	0440-8056	TABLET	500 mg	ORAL	ANDA	14 sections
Penicillin V Potasium	HUMAN PRESCRIPTION DRUG LABEL	1	0781-1205	TABLET	250 mg	ORAL	ANDA	15 sections
Penicillin V Potasium	HUMAN PRESCRIPTION DRUG LABEL	1	0781-1655	TABLET	500 mg	OROPHARYNGEAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	10544-075	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	10544-296	TABLET	250 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	10544-297	TABLET	500 mg	ORAL	ANDA	15 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	10544-500	TABLET	500 mg	ORAL	ANDA	15 sections
Penicillin V Potasium	HUMAN PRESCRIPTION DRUG LABEL	1	10544-975	TABLET	500 mg	ORAL	ANDA	16 sections
Penicillin V Potassium	Human Prescription Drug Label	1	16714-234	TABLET, FILM COATED	250 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	Human Prescription Drug Label	1	16714-235	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	21695-318	TABLET	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	21695-559	POWDER, FOR SOLUTION	250 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	21695-772	POWDER, FOR SOLUTION	125 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	33261-134	TABLET	250 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	33261-138	TABLET	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	42708-098	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	43063-557	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	43063-576	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	43063-614	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	43063-622	TABLET, FILM COATED	250 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	43063-680	TABLET, FILM COATED	500 mg	ORAL	ANDA	14 sections
Penicillin V Potassium	HUMAN PRESCRIPTION DRUG LABEL	1	43063-704	TABLET, FILM COATED	250 mg	ORAL	ANDA	14 sections