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)	0.45 mg/mL	Bocci G, Oprea TI, Benet LZ
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	238.91	26.83	61	4436	6337	63478188
Pancreatitis acute	166.16	26.83	65	4432	27101	63457424
Drug resistance	151.35	26.83	58	4439	22875	63461650
Pancreatitis	126.34	26.83	64	4433	48991	63435534
Thrombocytopenia	104.52	26.83	86	4411	151071	63333454
Hypofibrinogenaemia	95.37	26.83	21	4476	1149	63483376
Multiple organ dysfunction syndrome	82.84	26.83	51	4446	56701	63427824
Septic shock	61.38	26.83	45	4452	66584	63417941
Klebsiella infection	57.65	26.83	22	4475	8544	63475981
Sepsis	57.23	26.83	62	4435	153061	63331464
Coagulopathy	44.78	26.83	24	4473	20520	63464005
Hepatic failure	44.39	26.83	29	4468	35627	63448898
Biloma	44.09	26.83	7	4490	60	63484465
Morganella infection	43.55	26.83	10	4487	661	63483864
Adjusted calcium decreased	43.12	26.83	8	4489	182	63484343
Haemodynamic instability	42.44	26.83	18	4479	9172	63475353
Drug ineffective	41.43	26.83	164	4333	1044601	62439924
Haemostasis	40.93	26.83	8	4489	242	63484283
Vomiting	40.42	26.83	108	4389	559509	62925016
Globulins decreased	40.35	26.83	8	4489	261	63484264
Systemic inflammatory response syndrome	39.86	26.83	15	4482	5606	63478919
Acinetobacter infection	39.57	26.83	11	4486	1572	63482953
Deafness	39.20	26.83	21	4476	17936	63466589
Pain	38.43	26.83	4	4493	740624	62743901
Coma hepatic	37.96	26.83	9	4488	684	63483841
Blood urea increased	36.66	26.83	23	4474	26356	63458169
Blood fibrinogen decreased	36.10	26.83	9	4488	844	63483681
Wound haemorrhage	34.54	26.83	11	4486	2505	63482020
Immunosuppressant drug level increased	34.36	26.83	12	4485	3626	63480899
Hepatotoxicity	34.04	26.83	25	4472	37016	63447509
Multiple-drug resistance	33.79	26.83	13	4484	5157	63479368
Agranulocytosis	32.64	26.83	21	4476	25113	63459412
Enterococcal infection	31.74	26.83	14	4483	7834	63476691
Nausea	31.24	26.83	131	4366	854340	62630185
Renal failure	31.19	26.83	40	4457	117612	63366913
Off label use	30.81	26.83	111	4386	674351	62810174
Nephropathy toxic	29.22	26.83	14	4483	9465	63475060
Lipase increased	28.64	26.83	14	4483	9886	63474639
Escherichia infection	28.07	26.83	15	4482	12739	63471786
Acute kidney injury	27.77	26.83	59	4438	263356	63221169
Arthralgia	27.26	26.83	4	4493	569706	62914819
Graft versus host disease	27.15	26.83	12	4485	6751	63477774

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	196.11	26.84	70	5862	9412	34941587
Hypofibrinogenaemia	148.19	26.84	38	5894	1648	34949351
Septic shock	138.38	26.84	107	5825	71727	34879272
Drug resistance	136.85	26.84	73	5859	25854	34925145
Drug ineffective	133.82	26.84	259	5673	456492	34494507
Multiple organ dysfunction syndrome	107.56	26.84	95	5837	76471	34874528
Coagulopathy	102.36	26.84	55	5877	19734	34931265
Klebsiella infection	101.03	26.84	42	5890	8489	34942510
Treatment failure	79.99	26.84	65	5867	46632	34904367
Off label use	76.07	26.84	197	5735	419327	34531672
Thrombocytopenia	69.35	26.84	107	5825	156140	34794859
Sepsis	68.31	26.84	110	5822	166451	34784548
Enterococcal infection	65.94	26.84	32	5900	9274	34941725
Pancreatitis acute	63.12	26.84	46	5886	28095	34922904
Drug reaction with eosinophilia and systemic symptoms	56.59	26.84	46	5886	32966	34918033
Mycobacterium chelonae infection	55.45	26.84	15	5917	800	34950199
Deafness neurosensory	54.82	26.84	20	5912	2851	34948148
Blood fibrinogen decreased	53.66	26.84	16	5916	1214	34949785
Trichosporon infection	47.56	26.84	13	5919	721	34950278
Ototoxicity	42.81	26.84	15	5917	1902	34949097
Pancreatitis	42.43	26.84	42	5890	38849	34912150
Staphylococcal infection	40.69	26.84	38	5894	32722	34918277
Clostridium difficile colitis	40.53	26.84	28	5904	15702	34935297
Fungaemia	38.53	26.84	15	5917	2553	34948446
Candida infection	37.54	26.84	28	5904	17687	34933312
Gallstone ileus	36.85	26.84	6	5926	22	34950977
Myasthenia gravis crisis	35.55	26.84	10	5922	617	34950382
Product use in unapproved indication	34.33	26.84	67	5865	117432	34833567
Klebsiella bacteraemia	31.53	26.84	11	5921	1377	34949622
Flavobacterium infection	30.13	26.84	6	5926	80	34950919
Bilirubin conjugated increased	28.57	26.84	13	5919	3258	34947741
Geotrichum infection	28.40	26.84	8	5924	496	34950503
Multiple-drug resistance	28.29	26.84	15	5917	5224	34945775
Nausea	28.19	26.84	123	5809	339785	34611214
Anuria	27.97	26.84	19	5913	10366	34940633
Blood bilirubin increased	27.18	26.84	33	5899	38263	34912736
Acinetobacter test positive	26.84	26.84	6	5926	143	34950856

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	350.51	24.85	110	9386	14232	79720660
Drug resistance	247.50	24.85	114	9382	42099	79692793
Septic shock	191.72	24.85	140	9356	122661	79612231
Pancreatitis acute	186.45	24.85	99	9397	49505	79685387
Drug ineffective	167.95	24.85	384	9112	1080529	78654363
Hypofibrinogenaemia	165.23	24.85	40	9456	1962	79732930
Thrombocytopenia	157.29	24.85	175	9321	265084	79469808
Coagulopathy	155.77	24.85	79	9417	35927	79698965
Multiple organ dysfunction syndrome	152.16	24.85	121	9375	120125	79614767
Klebsiella infection	150.09	24.85	60	9436	15660	79719232
Sepsis	114.17	24.85	150	9346	269278	79465614
Off label use	106.17	24.85	290	9206	906925	78827967
Pancreatitis	104.19	24.85	77	9419	68498	79666394
Blood fibrinogen decreased	91.87	24.85	25	9471	1954	79732938
Acinetobacter infection	87.85	24.85	26	9470	2751	79732141
Enterococcal infection	87.65	24.85	41	9455	15619	79719273
Drug reaction with eosinophilia and systemic symptoms	73.45	24.85	61	9435	64183	79670709
Pain	59.74	24.85	7	9489	703795	79031097
Mycobacterium chelonae infection	56.47	24.85	18	9478	2438	79732454
Treatment failure	55.81	24.85	84	9412	170402	79564490
Multiple-drug resistance	55.36	24.85	25	9471	8783	79726109
Hepatotoxicity	51.01	24.85	45	9451	51307	79683585
Blood urea increased	48.95	24.85	43	9453	48747	79686145
Clostridium difficile colitis	48.43	24.85	36	9460	32247	79702645
Trichosporon infection	48.03	24.85	13	9483	995	79733897
Ototoxicity	47.58	24.85	17	9479	3257	79731635
Hepatic failure	46.11	24.85	46	9450	61166	79673726
Product use in unapproved indication	43.98	24.85	94	9402	250265	79484627
Pseudomonas infection	42.29	24.85	28	9468	20875	79714017
Morganella infection	42.06	24.85	12	9484	1115	79733777
Deafness neurosensory	41.52	24.85	19	9477	6879	79728013
Haemodynamic instability	39.38	24.85	25	9471	17357	79717535
Nephropathy toxic	38.07	24.85	26	9470	20393	79714499
Adjusted calcium decreased	37.62	24.85	8	9488	217	79734675
Fall	36.40	24.85	7	9489	487622	79247270
Renal failure	35.90	24.85	76	9420	200892	79534000
Staphylococcal infection	35.31	24.85	39	9457	58256	79676636
Headache	35.18	24.85	17	9479	653755	79081137
Pneumonia pseudomonal	34.70	24.85	16	9480	5895	79728997
Biloma	34.50	24.85	7	9489	150	79734742
Klebsiella bacteraemia	34.05	24.85	13	9483	2997	79731895
Activated partial thromboplastin time prolonged	33.58	24.85	21	9475	14207	79720685
Myasthenia gravis crisis	33.39	24.85	10	9486	1101	79733791
Coma hepatic	33.37	24.85	10	9486	1103	79733789
Lipase increased	33.17	24.85	22	9474	16444	79718448
Candida infection	33.07	24.85	31	9465	38183	79696709
Haemostasis	33.00	24.85	8	9488	394	79734498
Platelet count decreased	32.91	24.85	72	9424	194592	79540300
Dysbiosis	32.48	24.85	10	9486	1209	79733683
Fungaemia	31.96	24.85	14	9482	4577	79730315
Globulins decreased	31.74	24.85	8	9488	463	79734429
Electrocardiogram QT prolonged	31.64	24.85	46	9450	90340	79644552
Hepatitis cholestatic	31.57	24.85	20	9476	13832	79721060
Flavobacterium infection	31.17	24.85	6	9490	97	79734795
Hypertriglyceridaemia	30.56	24.85	19	9477	12721	79722171
Arthralgia	30.55	24.85	15	9481	571788	79163104
Aspergillus infection	30.16	24.85	22	9474	19139	79715753
Endocarditis	28.49	24.85	17	9479	10580	79724312
Immunosuppressant drug level increased	28.29	24.85	16	9480	9011	79725881
Mycobacterium abscessus infection	28.27	24.85	9	9487	1213	79733679
Fatigue	28.25	24.85	42	9454	929685	78805207
Acute kidney injury	27.92	24.85	129	9367	519275	79215617
Pneumonia klebsiella	27.56	24.85	13	9483	5041	79729851
Systemic inflammatory response syndrome	27.25	24.85	17	9479	11448	79723444
Procalcitonin increased	27.04	24.85	11	9485	2995	79731897
Escherichia infection	26.81	24.85	20	9476	17997	79716895
Wound haemorrhage	26.75	24.85	12	9484	4149	79730743
Geotrichum infection	25.93	24.85	8	9488	973	79733919
Acinetobacter test positive	25.57	24.85	6	9490	257	79734635
Drug ineffective for unapproved indication	25.52	24.85	31	9465	51207	79683685
Liver abscess	25.33	24.85	13	9483	6041	79728851
Cholestasis	25.10	24.85	31	9465	52078	79682814
Blood bilirubin increased	25.08	24.85	35	9461	66197	79668695
Eosinophilic pneumonia acute	25.05	24.85	8	9488	1090	79733802
Abdominal infection	25.04	24.85	11	9485	3618	79731274
Acinetobacter bacteraemia	25.00	24.85	6	9490	283	79734609

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	0008-4990	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
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	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	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