U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H17FN4O3
Molecular Weight 320.3189
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOXACIN

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(N3CCNCC3)C(F)=C2

InChI

InChIKey=IDYZIJYBMGIQMJ-UHFFFAOYSA-N
InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C15H17FN4O3
Molecular Weight 320.3189
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6226242 | https://www.ncbi.nlm.nih.gov/pubmed/8429114 | https://www.ncbi.nlm.nih.gov/pubmed/8494374

Enoxacin is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Enoxacin is bactericidal drugs, eradicating bacteria by interfering with DNA replication. Like other fluoroquinolones, enoxacin functions by inhibiting bacterial DNA gyrase and topoisomerase IV. The inhibition of these enzymes prevents bacterial DNA replication, transcription, repair and recombination. Enoxacin is active against many Gram-positive bacteria. After oral administration enoxacin is rapidly and well absorbed from the gastrointestinal tract. The antibiotic is widely distributed throughout the body and in the different biological tissues. Tissue concentrations often exceed serum concentrations. The binding of enoxacin to serum proteins is 35 to 40%. The serum elimination half-life, in subjects with normal renal function, is approximately 6 hours. Approximately 60% of an orally administered dose is excreted in the urine as unchanged drug within 24 hours. Enoxacin, like other fluoroquinolones, is known to trigger seizures or lower the seizure threshold. The compound should not be administered to patients with epilepsy or a personal history of previous convulsive attacks as may promote the onset of these disorders.

Originator

Curator's Comment: Enoxacin is a new pyridonecarboxylic acid derivative synthesized by Matsumoto et al.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PENETREX

Approved Use

INDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

Launch Date

1991
Curative
PENETREX

Approved Use

INDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

Launch Date

1991
Curative
PENETREX

Approved Use

INDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

Launch Date

1991
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.4 mg/L
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
4-OXO-ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.7 mg/L
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
4-OXO-ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
3.8 mg/L
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.58 mg/L
800 mg single, intravenous
dose: 800 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.02 mg/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.83 mg/L
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.8 mg/L
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
7.4 mg/L
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
25.75 mg × h/L
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
29.08 mg × h/L
800 mg single, intravenous
dose: 800 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.67 mg × h/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.35 mg × h/L
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
4-OXO-ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.9 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.9 h
800 mg single, intravenous
dose: 800 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.2 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.2 h
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.5 h
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
6 h
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
unhealthy, 41.9 years
n = 79
Health Status: unhealthy
Condition: cystitis
Age Group: 41.9 years
Sex: M+F
Population Size: 79
Sources:
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources:
unhealthy, 43.8 years
n = 75
Health Status: unhealthy
Condition: cystitis
Age Group: 43.8 years
Sex: M+F
Population Size: 75
Sources:
600 mg 3 times / day multiple, oral (max)
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
unhealthy, adult
n = 20060
Health Status: unhealthy
Condition: Gram-negative urinary tract pathogens
Age Group: adult
Sex: M+F
Population Size: 20060
Sources:
Other AEs: Gastrointestinal disorders, Epidermal and dermal conditions...
Other AEs:
Gastrointestinal disorders (1.3%)
Epidermal and dermal conditions (0.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Epidermal and dermal conditions 0.4%
600 mg 3 times / day multiple, oral (max)
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
unhealthy, adult
n = 20060
Health Status: unhealthy
Condition: Gram-negative urinary tract pathogens
Age Group: adult
Sex: M+F
Population Size: 20060
Sources:
Gastrointestinal disorders 1.3%
600 mg 3 times / day multiple, oral (max)
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
unhealthy, adult
n = 20060
Health Status: unhealthy
Condition: Gram-negative urinary tract pathogens
Age Group: adult
Sex: M+F
Population Size: 20060
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Enoxacin acute liver injury.
1992 May
Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry.
2002 Apr 5
Identification and characterization of a novel efflux-related multidrug resistance phenotype in Staphylococcus aureus.
2002 Dec
Spectrophotometric determination of enoxacin as ion-pairs with bromophenol blue and bromocresol purple in bulk and pharmaceutical dosage form.
2002 Jul 1
The expanding role of fluoroquinolones.
2002 Jul 8
Possible gatifloxacin-induced fulminant hepatic failure.
2002 Jul-Aug
[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration].
2002 Jun
[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies].
2002 Jun
Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin.
2002 Mar
Osteoadsorptive bisphosphonate derivatives of fluoroquinolone antibacterials.
2002 May 23
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation.
2002 May 27
Antituberculosis agents. III. In vitro evaluation of antimycobacterial activity and cytotoxicity of some N-piperazinyl quinolone derivatives.
2002 May-Jun
[The history of the development and changes of quinolone antibacterial agents].
2003
[Synthesis and antibacterial activity of pyridonecarboxylic acid derivatives containing 2-methyl-5-nitroimidazol].
2003 Apr
[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].
2003 Aug
Binding characteristics of fluoroquinolones to synthetic levodopa melanin.
2003 Aug
Corneal and scleral permeability of quinolones--a pharmacokinetics study.
2003 Dec
Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs.
2003 Dec
A randomized controlled trial (volunteer study) of sitafloxacin, enoxacin, levofloxacin and sparfloxacin phototoxicity.
2003 Dec
Dead bugs don't mutate: susceptibility issues in the emergence of bacterial resistance.
2003 Jan
Interference-free analysis using three-way fluorescence data and the parallel factor model. Determination of fluoroquinolone antibiotics in human serum.
2003 Jun 1
[Analysis of the response factors of different quinolones detected by evaporative light-scattering detector].
2003 Sep
Enoxacin trihydrate.
2004 Apr
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004 Apr
Comparative evaluation of antiproliferative activity and induction of apoptosis by some fluoroquinolones with a human non-small cell lung cancer cell line in culture.
2004 Apr-Jun
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin.
2004 Dec
Effects of eight antibacterial agents on cell survival and expression of epithelial-cell- or cell-adhesion-related genes in human gingival epithelial cells.
2004 Feb
Sensitivity and spectrum of bacterial isolates in infectious otitis externa.
2004 Mar
Spectroscopic properties of various quinolone antibiotics in aqueous-organic solvent mixtures.
2004 Nov-Dec
Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux.
2004 Nov-Dec
[Simultaneous determination of quinolones in foods by LC/MS/MS].
2004 Oct
Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods.
2005 Apr 4
HPLC determination of enoxacin, ciprofloxacin, norfloxacin and ofloxacin with photoinduced fluorimetric (PIF) detection and multiemission scanning: application to urine and serum.
2005 Aug 5
Selective action of fluoroquinolones against intracellular amastigotes of Leishmania (Viannia) panamensis in vitro.
2005 Dec
Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation.
2005 Jul 4
Flow-injection electrogenerated chemiluminescence determination of fluoroquinolones based on its sensitizing effect.
2005 Jul-Oct
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Interaction study between enoxacin and fluvoxamine.
2005 Jun
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.
2005 May
Vibrational spectroscopic characterization of fluoroquinolones.
2005 May
Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography.
2005 Nov
Bench-to-bedside review: antimicrobial utilization strategies aimed at preventing the emergence of bacterial resistance in the intensive care unit.
2005 Oct 5
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.
2006 Apr
Effects of Transcutol P on the corneal permeability of drugs and evaluation of its ocular irritation of rabbit eyes.
2006 Jan
Photophysics and photochemistry of nalidixic acid.
2006 Jan-Feb
A batch chemiluminescence determination of enoxacin using a tris-(1,10-phenanthroline)ruthenium(II)-cerium(IV) system.
2006 Jul
Quinolones for uncomplicated acute cystitis in women.
2006 Jul 19
[Study on interaction of caffeine and theophylline with bovine serum albumins].
2006 Mar
Electrochemiluminescence of terbium (III)-two fluoroquinolones-sodium sulfite system in aqueous solution.
2006 May 1
Induction of keratinocyte apoptosis by photosensitizing chemicals plus UVA.
2007 Feb
Patents

Sample Use Guides

Enoxacin should be taken at least one hour before or at least two hours after a meal. For treatment uncomplicated urethral or cervical gonorrhea: 400 mg single dose. For treatment uncomplicated urinary tract infections 200 mg q12h for 7 days. For treatment complicated urinary tract infections: 400 mg q12h for 14 days. Dosage should be adjusted in patients with a creatinine clearance value of 30 mL/min/1.73 m 2 or less.
Route of Administration: Oral
In Vitro Use Guide
The in vitro antibacterial activity of AT-2266 (Enoxacin ) was tested by the determination of minimal bactericidal concentrations (MBCs) and the reduction of viable cells during exposure to the drug for 24 h. MIC90s of AT-2266 for P. aeruginosa resistant to gentamicin and Enterobacteriaceae resistant to nalidixic acid were 3.13 and 12.5 mkg/ml, respectively
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:03:08 GMT 2023
Edited
by admin
on Sat Dec 16 18:03:08 GMT 2023
Record UNII
325OGW249P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENOXACIN
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-629661
Code English
Enoxacin [WHO-DD]
Common Name English
PD 107779
Code English
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
Systematic Name English
CI-919
Code English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)
Common Name English
AT-2266
Code English
ENOXACIN [MI]
Common Name English
1-ETHYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID
Systematic Name English
ENOXACIN [VANDF]
Common Name English
PD-107779
Code English
PENETREX
Brand Name English
ENOXACIN [USAN]
Common Name English
NSC-758416
Code English
ENOXACIN [ORANGE BOOK]
Common Name English
enoxacin [INN]
Common Name English
ENOXACIN [MART.]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/15/1459
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
WHO-VATC QJ01MA04
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
NCI_THESAURUS C795
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
WHO-ATC J01MA04
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1013
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
NSC
629661
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PRIMARY
NSC
758416
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PRIMARY
SMS_ID
100000080254
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
MESH
D015365
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PRIMARY
CAS
74011-58-8
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL826
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PRIMARY
INN
5351
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PRIMARY
USAN
U-65
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PRIMARY
FDA UNII
325OGW249P
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
NCI_THESAURUS
C65512
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
WIKIPEDIA
ENOXACIN
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
DRUG BANK
DB00467
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
LACTMED
Enoxacin
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
CHEBI
157175
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
IUPHAR
1157
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
PUBCHEM
3229
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PRIMARY
RXCUI
3925
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY RxNorm
EVMPD
SUB06540MIG
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PRIMARY
IUPHAR
316
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PRIMARY
EPA CompTox
DTXSID5022984
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY
MERCK INDEX
m4911
Created by admin on Sat Dec 16 18:03:08 GMT 2023 , Edited by admin on Sat Dec 16 18:03:08 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY