Page last updated: 2024-11-05

caprolactam

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Caprolactam is a cyclic lactam, specifically a seven-membered lactam. It is a colorless solid that is an important precursor for the production of nylon-6. Caprolactam is synthesized through the Beckmann rearrangement of cyclohexanone oxime. Caprolactam undergoes polymerization to form nylon-6, a synthetic polymer with a wide range of applications due to its strength, durability, and versatility. Caprolactam is widely studied for its importance in the production of nylon-6, a key material in various industries. Research focuses on optimizing the synthesis of caprolactam, exploring new catalysts and reaction conditions to improve efficiency and reduce environmental impact.'

Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID7768
CHEMBL ID276218
CHEBI ID28579
SCHEMBL ID19610
MeSH IDM0003306

Synonyms (233)

Synonym
9012-16-2
nsc-4977
nsc4977
CHEBI:28579 ,
kaprolaktam
2-ketohexamethyleneimine
nsc-25536
nsc25536
hexanolactam
6-aminocaproic acid lactam
2h-azepin-7-one,hexahydro
e-caprolactum
hexanoic acid-6-amino-,lactam
hexannic acid
omega-caprolactum
6-aminohexanoic acid cyclic lactam
C0432
gamma-caprolactam
perhydroazepin-2-one
cm 1041
akulon
itamide 35
nylon cm 1031
kapron b
plaskon 8201
itamid 250
cm 1001
cm 1031
ertalon 6sa
miramid h 2
amilan cm 1001g
zytel 211
durethan bkv 30h
itamide 350
itamide 25
ultramid b 3
plaskon 8205
tarlon xb
amilan cm 1001
tarlon x-a
cm 1011
ube 1022b
capron 8250
kaprolon b
durethan bk
dull 704
itamid
maranyl f 114
ultramid b 4
kaprolon
plaskon 8201hs
tarnamid t 2
orgamide
danamid
chemlon
capron 8256
capran 77c
spencer 401
amilan cm 1001c
maranyl f 124
caprolon b
ultramid b 5
pk 4
ultramid bmk
relon p
nylon x 1051
vidlon
grilon
itamide 250
tarnamid t
capran 80
amilan cm 1011
plaskon 8202c
sipas 60
capron 8253
durethan bkv 55h
capron 8252
spencer 601
alkamid
torayca n 6
metamid
itamide 250g
capron b
kapron a
plaskon 201
capron
plaskon 8207
plaskon 8252
kaprolit b
capron gr 8258
plaskin 8200
nylon a1035sf
durethan bk 30s
maranyl f 500
itamide s
kapron
capron gr 8256
orgamid rmnocd
miramid wm 55
caprolon v
plaskon xp 607
kaprolit
renyl mv
widlon
2-azacycloheptanone
caprolactam monomer
2-ketohexamethylenimine
105-60-2
hexahydro-2h-azepin-2-one
wln: t7mvtj
nsc-117393
nsc117393
hexahydro-2-azepinone
1-aza-2-cycloheptanone
6-hexanelactam
.omega.-caprolactam
hexanonisoxim
6-caprolactam
hexanoic acid, lactam
caprolattame
nci-c50646
2h-azepin-7-one, hexahydro-
cyclohexanone iso-oxime
caprolactam
2-perhydroazepinone
1,6-hexolactam
e-kaprolaktam
2h-azepin-2-one, hexahydro-
hexanone isoxime
hexanoic acid, cyclic lactam
aminocaproic lactam
epsylon kaprolaktam
hexamethylenimine, 2-oxo-
.epsilon.-caprolactam
2-oxohexamethylenimine
inchi=1/c6h11no/c8-6-4-2-1-3-5-7-6/h1-5h2,(h,7,8
azepan-2-one
hexanoic acid,6-amino,lactam e-caprolactam
2-oxohexamethyleneimine
nsc 117393
capron pk4
hexanoic acid, 6-amino-, lactam
kapromine
hsdb 187
hexanoic acid, 6-amino-, cyclic lactam
stilon
ai3-14515
epsylon kaprolaktam [polish]
caprolattame [french]
extrom 6n
ccris 119
e-kaprolaktam [czech]
hexanonisoxim [german]
A1030 ,
caprolactam dust and vapor
einecs 203-313-2
1,6-hexalactam
brn 0106934
C06593
epsilon-caprolactam
epsilon-caprolactam, 99%
STK378587
hexanoic acid-6-amino-lactam
e-caprolactam
cyclohexanoneisooxime
2-azepinone, hexahydro-, (z)-
BMSE000372
cis-hexahydro-2-azepinone
aza-2-cycloheptanone
CHEMBL276218
AKOS000119969
A23500
NCGC00247913-02
NCGC00247913-01
niosh/cm3900000
CM39000000
cas-105-60-2
NCGC00259751-01
NCGC00253933-01
tox21_300163
dtxsid4020240 ,
tox21_202202
dtxcid00240
AM802872
ec 203-313-2
6879x594z8 ,
5-21-06-00444 (beilstein handbook reference)
unii-6879x594z8
FT-0625676
FT-0623443
caprolactam [hsdb]
caprolactam [usp-rs]
fema no. 4235
zinc acexamate impurity d [ep impurity]
1,6-hexalactam [fhfi]
caprolactam [iarc]
caprolactam [mi]
SCHEMBL19610
epsilon caprolactam
hexahydroazepin-2-one
6-hexanolactam
azacycloheptane-2-one
azacycloheptan-2-one
hexano-6-lactam
tarnamid t 27
stylon
atm 2(nylon)
capron 8257
2-azepanone #
steelon
6-aminohexanoic acid lactam
STR02412
mfcd00006936
J-510225
epsilon-caprolactam, analytical standard
F0001-0110
caprolactim
hexahydro 2h azepin 2 one
lactam, aminocaproic
Q409397
epsilon-caprolactam-d10
caprolactam,(s)
D70254
?2-oxohexamethylenimine
EN300-19667
epsilon -caprolactam
hexamethylenimine,2-oxo-
hexahydro-2h-azepine-2-one
caprolactam (iarc)
zinc acexamate impurity d (ep impurity)
caprolactam (usp-rs)
6-caprolactan
2h-azepin-2-one,hexahydro

Research Excerpts

Overview

Caprolactam is a monomer used for the synthesis of nylon-6. It is an important industrial chemical with a relatively low human toxicity. Of importance is the irritations that occur after exposure to caprolacts.

ExcerptReferenceRelevance
"Caprolactam (CPL) is an important chemical raw material. "( [Determination of the key impurity in caprolactam produced from a combined process by gas chromatography-mass spectroscopy].
Han, J, 2019
)
2.23
"Caprolactam is a monomer used for the synthesis of nylon-6, and a recombinant microbial strain for biobased production of nylon-6 was recently developed. "( Artificial Caprolactam-Specific Riboswitch as an Intracellular Metabolite Sensor.
Im, DK; Jang, S; Jung, GY; Kang, TJ; Oh, MK, 2019
)
2.35
"ε-Caprolactam is an important industrial chemical with a relatively low human toxicity; of importance is the irritations that occur after exposure to ε-caprolactam as aerosols or vapors."( Exposure study to examine chemosensory effects of ɛ-caprolactam in healthy men and women.
Bruckner, T; Triebig, G; Triebig-Heller, I, 2016
)
1.41

Toxicity

ExcerptReferenceRelevance
" The keratinization of the metaplastic epithelium in the larynx was considered to be an adverse effect."( Subchronic inhalation toxicity study of caprolactam (with a 4-week recovery) in the rat via whole-body exposures.
Bolte, HF; Hoffman, GM; Kayser, M; Parod, RJ; Reinhold, RW; Rinehart, WE; Rusch, GM, 1998
)
0.57

Bioavailability

ExcerptReferenceRelevance
" Relative bioavailability was significantly increased with Eudragit nanoparticles compared to the nifedipine/PEG solution."( The antihypertensive effect of orally administered nifedipine-loaded nanoparticles in spontaneously hypertensive rats.
Atkinson, J; Fluckiger, L; Hoffman, M; Kim, YI; Lartaud-Idjouadiene, I; Maincent, P, 1997
)
0.3
" Two compounds, 13c and 13j, were found to have good oral bioavailability (>50%) in rats when administered as prodrugs."( Synthesis and evaluation of unsaturated caprolactams as interleukin-1beta converting enzyme (ICE) inhibitors.
Baize, MW; Belkin, M; Buchalova, M; Cruze, CA; De, B; Demuth, TP; Ellis, CD; Fancher, AN; Laufersweiler, MC; Lu, W; O'Neil, SV; Oppong, KA; Schwecke, WP; Soper, DL; Suchanek, MK; Wang, RL; Wang, Y; Wos, JA, 2007
)
0.61
" The phenylimidazolinone privileged structure gave additional potency enhancements, as 24 showed good potency in both CGRP binding (K(i)=2 nM) and cAMP (IC(50)=4 nM) assays and was orally bioavailable in rats (27%)."( Caprolactams as potent CGRP receptor antagonists for the treatment of migraine.
Burgey, CS; Graham, SL; Kane, SA; Koblan, KS; Mosser, SD; Nguyen, DN; Paone, DV; Rutledge, RZ; Salvatore, CA; Shaw, AW; Stump, CA; Vacca, JP; Williams, TM, 2007
)
1.78
" The developed and validated method was successfully applied to relative bioavailability study for the preclinical evaluation of a new injectable DTX-sulfobutyl ether beta-cyclodextrin (DTX-SBE-beta-CD) inclusion complex freeze-dried powder (test preparation), compared with the reference preparation (DTX injection, Taxotere) in healthy rabbits."( Development and validation of a nylon6 nanofibers mat-based SPE coupled with HPLC method for the determination of docetaxel in rabbit plasma and its application to the relative bioavailability study.
Gu, Z; Shen, Y; Wang, M; Xu, Q; Xu, S; Yin, X; Zhang, L; Zhang, N, 2010
)
0.36
" The heating ability of MCP nanogels was calculated to be ∼204W/g for the concentration of 2mg/mL using time-dependent Specific Absorption Rate (SAR) method."( Dual responsive magnetic composite nanogels for thermo-chemotherapy.
Arunkumar, P; Bahadur, D; Indulekha, S; Srivastava, R, 2017
)
0.46
" Cell viability of assay was implemented to determination of biocompatibility, bioavailability and therapeutic potency of nano-complexes on different cancer and normal cell lines."( Synthesis and in vitro study of modified chitosan-polycaprolactam nanocomplex as delivery system.
Bidaki, K; Mohammadnejad, J; Narmani, A; Rezvani, M, 2018
)
0.73
"Maintaining a supersaturated drug solution after the dissolution of the solid dispersions of water insoluble drugs continues to be a great challenge and is important to the oral bioavailability enhancement of hardly soluble drugs."( Tri-block polymer with interfacial layer formation ability and its use in maintaining supersaturated drug solution after dissolution of solid dispersions.
Fu, JJ; Liu, CC, 2018
)
0.48
"The tri-block polymer was not only able to stabilize the supersaturated drug solution of solid dispersions to enhance the oral bioavailability of hardly soluble drugs, but is also a potential candidate to construct micelles for systemic administration, due to the good compatibility and organic solvents free micelle formation procedure."( Tri-block polymer with interfacial layer formation ability and its use in maintaining supersaturated drug solution after dissolution of solid dispersions.
Fu, JJ; Liu, CC, 2018
)
0.48
" The impurity contains strong chromophores and severely impacted the UV absorption rate of the CPL product."( [Determination of the key impurity in caprolactam produced from a combined process by gas chromatography-mass spectroscopy].
Han, J, 2019
)
0.78

Dosage Studied

4,6,6-Trimethylcaprolactam antagonised GABAA receptor-mediated contractile responses in guinea-pig isolated ileum. In rats dosed on days 6-15 of gestation with 100, 500 or 1000 mg/kg/day, the maternal survival rate was significantly lower in the high-dose group.

ExcerptRelevanceReference
"4,6,6-Trimethylcaprolactam antagonised GABAA receptor-mediated contractile responses in guinea-pig isolated ileum, displacing the GABA dose-response curve to the right in a non-parallel manner, and causing a depression of the maximum response."( Caprolactam-barbiturate interaction at the GABAA receptor complex in the guinea-pig intestine.
Kerr, DI; Ong, J; Prager, RH; Ward, DA, 1986
)
2.07
" In rats dosed on days 6-15 of gestation with 100, 500 or 1000 mg/kg/day of caprolactam, the maternal survival rate was significantly lower in the high-dose group and implantation efficiencies were slightly lower in the 100 and 1000 mg/groups (but not the 500 mg/kg) than in the control."( Developmental toxicity studies of caprolactam in the rat and rabbit.
Colpean, BR; Gad, SC; Robinson, K; Serota, DG, 1987
)
0.78
" All of the nanoparticle dosage forms decreased Cmax and increased Tmax and the mean residence time (MRT) values."( The antihypertensive effect of orally administered nifedipine-loaded nanoparticles in spontaneously hypertensive rats.
Atkinson, J; Fluckiger, L; Hoffman, M; Kim, YI; Lartaud-Idjouadiene, I; Maincent, P, 1997
)
0.3
" Thirty-two bird groups (sexes equal) of adult mallards were dosed orally with eight #4 steel shot (control), eight #4 tungsten-iron shot, or eight #4 tungsten-polymer shot on days 0, 30, 60, 90, and 120 of a 150-day trial (26 January 1998 to 25 June 1998)."( Health effects following chronic dosing with tungsten-iron and tungsten-polymer shot in adult game-farm mallards.
Aulerich, RJ; Balander, RJ; Bursian, SJ; Fitzgerald, SD; Mitchell, RR; Powell, DC; Stevens, W; Stickle, RL; Tempelman, RJ, 2001
)
0.31
" Fish and Wildlife Service required a chronic dosing study that assessed the health and reproductive effects of tungsten-iron and tungsten-polymer shot in adult game-farm mallards (Anas platyrhynchos) prior to granting permanent approval of the shot for waterfowl hunting."( Hematological effects and metal residue concentrations following chronic dosing with tungsten-iron and tungsten-polymer shot in adult game-farm mallards.
Aulerich, RJ; Balander, RJ; Bursian, SJ; Cray, C; Fitzgerald, SD; Mitchell, RR; Powell, DC; Stevens, W; Tempelman, RJ, 2001
)
0.31
" Sixteen male and 16 female adult mallards were dosed orally with eight #4 steel shot (control), eight #4 tungsten-iron shot, or eight #4 tungsten-polymer shot on days 0, 30, 60, 90, and 120 of a 150-day trial (26 January 1998 to 25 June 1998)."( Reproductive effects and duckling survivability following chronic dosing with tungsten-iron and tungsten-polymer shot in adult game-farm mallards.
Aulerich, RJ; Balander, RJ; Bursia, SJ; Fitzgerald, SD; Mitchell, RR; Powell, DC; Stevens, W; Tempelmen, RJ, 2001
)
0.31
"Six hour exposures to epsilon-caprolactam revealed no significant dose-response relationship concerning blink frequency, nasal resistance and redness of the bulbar conjunctiva."( Exposure study on chemosensory effects of epsilon-caprolactam in the low concentration range.
Triebig, G; Ziegler, AE; Zimmer, H, 2008
)
0.89
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human blood serum metaboliteAny metabolite (endogenous or exogenous) found in human blood serum samples.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
caprolactamsA lactam in which the amide bond is contained within a seven-membered ring, which includes the amide nitrogen and the carbonyl carbon.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
nylon-6 oligomer degradation115

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency6.48850.006038.004119,952.5996AID1159523
SMAD family member 2Homo sapiens (human)Potency61.81830.173734.304761.8120AID1346859
SMAD family member 3Homo sapiens (human)Potency61.81830.173734.304761.8120AID1346859
GLI family zinc finger 3Homo sapiens (human)Potency1.53870.000714.592883.7951AID1259369
AR proteinHomo sapiens (human)Potency20.51830.000221.22318,912.5098AID1259247
caspase 7, apoptosis-related cysteine proteaseHomo sapiens (human)Potency21.73410.013326.981070.7614AID1346978
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency9.70830.001022.650876.6163AID1224893
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency9.16520.003041.611522,387.1992AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency3.09830.000817.505159.3239AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency26.21710.001530.607315,848.9004AID1259401; AID1259403
estrogen nuclear receptor alphaHomo sapiens (human)Potency18.66030.000229.305416,493.5996AID1259248; AID743069
caspase-3Homo sapiens (human)Potency21.73410.013326.981070.7614AID1346978
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency19.54870.057821.109761.2679AID1159528
Histone H2A.xCricetulus griseus (Chinese hamster)Potency9.53710.039147.5451146.8240AID1224896
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID71833Ability to displace radioligand [35S]TBPS from Gamma-aminobutyric acid A receptor binding site in rat brain membranes1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID70691Concentration producing the maximum percentage of benzidine-positive cells after 6-days of continuous exposure in murine leukemia cells.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID113778Anticonvulsant activity expressed as dose at which 50% of the mice were protected from clonic seizures induced by pentylenetetrazole (85 mg/Kg); cytotoxicity observed at 300 mg/kg1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID70690Cell growth was measured on day 6 after murine erythroleukemia cells were exposed at a cell concentration of 1*10e5 cells/mL.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID226512Protective Index (PI) determined as the ratio of toxic dose (TD50) and effective dose (ED50 (PTZ))1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID212342Neurotoxicity was evaluated by a rotarod test1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID25749Compound was evaluated for the second order hydrolysis rate constant2000Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22
Hydrolytic stability versus ring size in lactams: implications for the development of lactam antibiotics and other serine protease inhibitors.
AID227699Virtual screen for compounds with anticonvulsant activity2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.
AID70689Cell growth was measured on day 3, after murine erythroleukemia cells were exposed at a cell concentration of 1*10e5 cells/mL.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID70688Percentage of benzidine-positive murine erythroleukemia cells on day 6.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID226511Protective Index (PI) determined as the ratio of toxic dose (TD50) and effective dose (ED50 (MES))1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID113779Anticonvulsant activity expressed as dose at which 50% of the mice were protected from tonic hindlimb seizures induced by maximal electroshock (MES)1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (692)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990216 (31.21)18.7374
1990's47 (6.79)18.2507
2000's125 (18.06)29.6817
2010's249 (35.98)24.3611
2020's55 (7.95)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 64.04

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index64.04 (24.57)
Research Supply Index6.65 (2.92)
Research Growth Index4.84 (4.65)
Search Engine Demand Index110.50 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (64.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (0.79%)5.53%
Reviews17 (2.23%)6.00%
Case Studies25 (3.28%)4.05%
Observational1 (0.13%)0.25%
Other714 (93.58%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]