tigecycline 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, protein-synthesis inhibitors, tetracycline derivatives	2661	220620-09-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: CL-331002 CL 331002 tigecycline tygacil glycylcycline	Tigecycline inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. In general, tigecycline is considered bacteriostatic; however, tigecycline has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila. Molecular weight: 585.66 Formula: C29H39N5O8 CLOGP: -0.19 LIPINSKI: 3 HAC: 13 HDO: 7 TPSA: 205.76 ALOGS: -3.11 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

CL-331002
CL 331002
tigecycline
tygacil
glycylcycline

Tigecycline inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. In general, tigecycline is considered bacteriostatic; however, tigecycline has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila.

Molecular weight: 585.66
Formula: C29H39N5O8
CLOGP: -0.19
LIPINSKI: 3
HAC: 13
HDO: 7
TPSA: 205.76
ALOGS: -3.11
ROTB: 7

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.10	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	295 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	22 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	0 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	12 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	3.80 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.20 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	48 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
June 15, 2005	FDA	PF PRISM CV

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
Pathogen resistance	222.08	27.95	57	3790	5632	50595645
Pancreatitis acute	159.37	27.95	62	3785	23750	50577527
Pancreatitis	124.70	27.95	62	3785	42552	50558725
Drug resistance	111.47	27.95	45	3802	18944	50582333
Hypofibrinogenaemia	84.02	27.95	19	3828	1093	50600184
Thrombocytopenia	80.49	27.95	71	3776	127602	50473675
Multiple organ dysfunction syndrome	65.05	27.95	43	3804	50294	50550983
Sepsis	52.00	27.95	57	3790	132868	50468409
Septic shock	48.89	27.95	38	3809	57137	50544140
Klebsiella infection	45.48	27.95	18	3829	7176	50594101
Adjusted calcium decreased	45.35	27.95	8	3839	126	50601151
Morganella infection	44.21	27.95	10	3837	575	50600702
Biloma	43.59	27.95	7	3840	60	50601217
Haemodynamic instability	43.57	27.95	18	3829	8006	50593271
Globulins decreased	41.39	27.95	8	3839	212	50601065
Haemostasis	40.46	27.95	8	3839	239	50601038
Systemic inflammatory response syndrome	40.40	27.95	15	3832	5034	50596243
Coma hepatic	38.38	27.95	9	3838	607	50600670
Vomiting	38.38	27.95	98	3749	460660	50140617
Deafness	37.63	27.95	20	3827	15671	50585606
Blood urea increased	37.54	27.95	23	3824	23562	50577715
Hepatotoxicity	36.95	27.95	24	3823	27202	50574075
Wound haemorrhage	35.79	27.95	11	3836	2079	50599198
Immunosuppressant drug level increased	35.49	27.95	12	3835	3070	50598207
Multiple-drug resistance	34.63	27.95	12	3835	3302	50597975
Hepatic failure	33.24	27.95	24	3823	32259	50569018
Pain	33.17	27.95	3	3844	578900	50022377
Blood fibrinogen decreased	32.74	27.95	8	3839	643	50600634
Drug ineffective	32.42	27.95	135	3712	819198	49782079
Agranulocytosis	31.84	27.95	20	3827	21401	50579876
Acinetobacter infection	30.88	27.95	9	3838	1418	50599859
Nephropathy toxic	30.49	27.95	14	3833	8015	50593262
Nausea	30.05	27.95	119	3728	705279	49895998
Enterococcal infection	29.28	27.95	13	3834	6885	50594392
Escherichia infection	29.24	27.95	15	3832	10926	50590351

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
Pathogen resistance	189.86	25.99	66	5056	8050	29561355
Hypofibrinogenaemia	146.84	25.99	37	5085	1464	29567941
Septic shock	138.36	25.99	102	5020	62458	29506947
Drug ineffective	131.25	25.99	228	4894	362942	29206463
Drug resistance	110.71	25.99	60	5062	21480	29547925
Multiple organ dysfunction syndrome	98.75	25.99	84	5038	63032	29506373
Klebsiella infection	95.88	25.99	39	5083	7310	29562095
Sepsis	72.25	25.99	105	5017	142577	29426828
Thrombocytopenia	66.47	25.99	98	5024	134725	29434680
Treatment failure	65.67	25.99	53	5069	36886	29532519
Enterococcal infection	59.75	25.99	29	5093	8239	29561166
Deafness neurosensory	56.53	25.99	20	5102	2558	29566847
Mycobacterium chelonae infection	54.58	25.99	14	5108	594	29568811
Pancreatitis acute	49.82	25.99	38	5084	24347	29545058
Ototoxicity	45.50	25.99	15	5107	1550	29567855
Pancreatitis	44.05	25.99	41	5081	34473	29534932
Fungaemia	40.62	25.99	15	5107	2166	29567239
Clostridium difficile colitis	39.53	25.99	26	5096	13186	29556219
Myasthenia gravis crisis	37.77	25.99	10	5112	481	29568924
Coagulopathy	36.77	25.99	28	5094	17879	29551526
Gallstone ileus	36.73	25.99	6	5116	22	29569383
Candida infection	36.19	25.99	26	5096	15199	29554206
Off label use	34.40	25.99	122	5000	300678	29268727
Product use in unapproved indication	34.14	25.99	57	5065	86818	29482587
Multiple-drug resistance	32.20	25.99	15	5107	3885	29565520
Staphylococcal infection	32.13	25.99	32	5090	29208	29540197
Flavobacterium infection	30.01	25.99	6	5116	80	29569325
Nausea	29.41	25.99	113	5009	289142	29280263
Geotrichum infection	29.22	25.99	8	5114	437	29568968
Anuria	29.08	25.99	19	5103	9522	29559883
Drug reaction with eosinophilia and systemic symptoms	27.78	25.99	29	5093	27963	29541442
Acoustic neuroma	26.57	25.99	6	5116	147	29569258

FDA Adverse Event Reporting System (Geriatric)

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
Pathogen resistance	325.71	25.64	102	7989	12441	64478200
Drug resistance	201.71	25.64	95	7996	35007	64455634
Septic shock	176.58	25.64	128	7963	105309	64385332
Pancreatitis acute	166.61	25.64	89	8002	42766	64447875
Hypofibrinogenaemia	152.43	25.64	37	8054	1741	64488900
Drug ineffective	151.72	25.64	327	7764	839920	63650721
Klebsiella infection	135.68	25.64	54	8037	13227	64477414
Thrombocytopenia	133.76	25.64	152	7939	223649	64266992
Multiple organ dysfunction syndrome	125.64	25.64	103	7988	101310	64389331
Sepsis	112.18	25.64	141	7950	230200	64260441
Pancreatitis	105.68	25.64	75	8016	59532	64431109
Enterococcal infection	77.94	25.64	37	8054	13829	64476812
Acinetobacter infection	72.48	25.64	22	8069	2407	64488234
Coagulopathy	67.98	25.64	45	8046	31875	64458766
Multiple-drug resistance	58.01	25.64	24	8067	6478	64484163
Hepatotoxicity	56.68	25.64	44	8047	39918	64450723
Blood fibrinogen decreased	55.74	25.64	16	8075	1442	64489199
Mycobacterium chelonae infection	53.83	25.64	17	8074	2120	64488521
Off label use	53.34	25.64	187	7904	632619	63858022
Blood urea increased	50.75	25.64	43	8048	44110	64446531
Ototoxicity	49.78	25.64	17	8074	2706	64487935
Treatment failure	49.66	25.64	67	8024	116749	64373892
Pain	48.99	25.64	6	8085	553505	63937136
Clostridium difficile colitis	45.32	25.64	33	8058	27190	64463451
Morganella infection	42.79	25.64	12	8079	994	64489647
Deafness neurosensory	42.01	25.64	19	8072	6355	64484286
Haemodynamic instability	41.72	25.64	25	8066	14887	64475754
Pseudomonas infection	39.98	25.64	26	8065	17857	64472784
Adjusted calcium decreased	39.73	25.64	8	8083	156	64490485
Drug reaction with eosinophilia and systemic symptoms	39.53	25.64	41	8050	54176	64436465
Product use in unapproved indication	38.78	25.64	75	8016	176543	64314098
Nephropathy toxic	38.02	25.64	25	8066	17489	64473152
Pneumonia pseudomonal	36.77	25.64	16	8075	4887	64485754
Fall	35.69	25.64	5	8086	416821	64073820
Haemostasis	35.52	25.64	8	8083	270	64490371
Myasthenia gravis crisis	35.14	25.64	10	8081	874	64489767
Biloma	34.14	25.64	7	8084	150	64490491
Fungaemia	33.86	25.64	14	8077	3771	64486870
Coma hepatic	33.80	25.64	10	8081	1002	64489639
Globulins decreased	33.16	25.64	8	8083	366	64490275
Klebsiella bacteraemia	32.83	25.64	12	8079	2328	64488313
Headache	32.39	25.64	13	8078	529454	63961187
Aspergillus infection	32.24	25.64	22	8069	16357	64474284
Renal failure	31.48	25.64	70	8021	181618	64309023
Flavobacterium infection	31.22	25.64	6	8085	91	64490550
Immunosuppressant drug level increased	30.79	25.64	16	8075	7243	64483398
Hepatitis cholestatic	30.47	25.64	19	8072	12136	64478505
Hepatic failure	30.22	25.64	36	8055	55358	64435283
Endocarditis	29.59	25.64	17	8074	9361	64481280
Staphylococcal infection	29.41	25.64	34	8057	50644	64439997
Hypertriglyceridaemia	29.32	25.64	18	8073	11187	64479454
Escherichia infection	28.97	25.64	20	8071	15148	64475493
Candida infection	28.93	25.64	27	8064	31392	64459249
Acute kidney injury	28.85	25.64	122	7969	449118	64041523
Electrocardiogram QT prolonged	28.45	25.64	42	8049	79406	64411235
Wound haemorrhage	28.37	25.64	12	8079	3419	64487222
Systemic inflammatory response syndrome	28.22	25.64	17	8074	10218	64480423
Abdominal infection	26.73	25.64	11	8080	2929	64487712
Pneumonia klebsiella	26.50	25.64	12	8079	4025	64486616
Liver abscess	26.37	25.64	13	8078	5267	64485374
Acinetobacter bacteraemia	26.35	25.64	6	8085	213	64490428
Eosinophilic pneumonia acute	26.32	25.64	8	8083	879	64489762
Geotrichum infection	26.05	25.64	8	8083	910	64489731
Acoustic neuroma	25.88	25.64	6	8085	231	64490410

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J01AA12	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE TETRACYCLINES Tetracyclines
FDA CS	M0021223	Tetracyclines
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D011500	Protein Synthesis Inhibitors
FDA EPC	N0000175938	Tetracycline-class Antibacterial

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Pneumonia due to Streptococcus	indication	34020007
Haemophilus influenzae pneumonia	indication	70036007
Abdominal abscess	indication	75100008
Infectious disease of abdomen	indication	128070006
Complicated appendicitis	indication	418171008
Complicated Skin and Skin Structure E. Coli Infection	indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection	indication
Complicated Skin and Skin Structure Infection	indication
Complicated Skin and Skin Structure Streptococcus Pyogenes Infection	indication
Legionella Pneumophila Pneumonia	indication
Complicated Bacterial Peritonitis	indication
Complicated Skin and Skin Structure Enterococcus Faecalis Infection	indication
Complicated Skin and Skin Structure Streptococcus Agalactiae Infection	indication
Hyperbilirubinemia	contraindication	14783006	DOID:2741
Gastrointestinal perforation	contraindication	51875005
Hepatic failure	contraindication	59927004
Pancreatitis	contraindication	75694006	DOID:4989
Pregnancy, function	contraindication	289908002
Pseudomembranous enterocolitis	contraindication	397683000
Antibiotic-Induced Hypoprothrombinemia	contraindication

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.13	acidic
pKa2	8.64	acidic
pKa3	11.14	acidic
pKa4	11.96	acidic
pKa5	13.08	acidic
pKa6	13.93	acidic
pKa7	9.41	Basic
pKa8	7.96	Basic
pKa9	7.31	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

ID	Source
4024922	VUID
N0000171604	NUI
D01079	KEGG_DRUG
4024922	VANDF
C1260298	UMLSCUI
CHEBI:142708	CHEBI
T1C	PDB_CHEM_ID
CHEMBL376140	ChEMBL_ID
D000078304	MESH_DESCRIPTOR_UI
DB00560	DRUGBANK_ID
C087533	MESH_SUPPLEMENTAL_RECORD_UI
10929	IUPHAR_LIGAND_ID
8115	INN_ID
70JE2N95KR	UNII
54686904	PUBCHEM_CID
384455	RXNORM
20166	MMSL
230306	MMSL
69774	MMSL
d05537	MMSL
010833	NDDF
418313005	SNOMEDCT_US
418631002	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Tygacil	HUMAN PRESCRIPTION DRUG LABEL	1	0008-4990	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	33 sections
Tygacil	HUMAN PRESCRIPTION DRUG LABEL	1	0008-4994	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	30 sections
Tigecycline	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3481	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	26 sections
TIGECYCLINE	HUMAN PRESCRIPTION DRUG LABEL	1	16729-364	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	31 sections
Tigecycline	Human Prescription Drug Label	1	55150-228	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Tigecycline	Human Prescription Drug Label	1	55150-228	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Tigecycline	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6098	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Tigecycline	Human Prescription Drug Label	1	63323-960	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	27 sections
Tigecycline	HUMAN PRESCRIPTION DRUG LABEL	1	70121-1647	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	22 sections
Tigecycline	HUMAN PRESCRIPTION DRUG LABEL	1	70594-035	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	33 sections
Tigecycline	HUMAN PRESCRIPTION DRUG LABEL	1	71288-019	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	30 sections