Page last updated: 2024-11-05

cyclopropane

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

Description

cyclopropane : A cycloalkane composed of three carbon atoms to form a ring. [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 CID6351
CHEMBL ID1796999
CHEBI ID30365
MeSH IDM0097155

Synonyms (43)

Synonym
cyclopropan
cyclopropane
CHEBI:30365 ,
zyklopropan
75-19-4
ciclopropano
trimethylene
cyclopropanum
cyclopropane (usp/inn)
D03627
rc 270
hsdb 812
trimethylene (cyclic)
ciclopropano [inn-spanish]
cyclopropane [inn]
cyclopropane [anaesthetics, volatile]
einecs 200-847-8
cyclopropanum [inn-latin]
un1027
inchi=1/c3h6/c1-2-3-1/h1-3h
cyclopropane, >=99%
CHEMBL1796999
unii-99tb643425
99tb643425 ,
cyclopropane [un1027] [flammable gas]
cyclopropane [usp:inn]
AKOS015915611
cyclopropane [who-dd]
cyclopropane [hsdb]
cyclopropane [mi]
cyclopropane [usp impurity]
cyclopropane [mart.]
DTXSID4058786 ,
cyclopropnane
un 1027
DB13984
mfcd00001268
Q80250
cyclopropane, (liquefied)
cyclopropane, liquefied
dtxcid1047734
cyclopropane (usp impurity)
cyclopropane (mart.)

Research Excerpts

Overview

Cyclopropane rings are an important structural motif frequently found in many natural products and pharmaceuticals.

ExcerptReferenceRelevance
"Cyclopropane rings are an important structural motif frequently found in many natural products and pharmaceuticals. "( Biocatalytic Asymmetric Cyclopropanations via Enzyme-Bound Iminium Ion Intermediates.
Kunzendorf, A; Poelarends, GJ; Saifuddin, M; Saravanan, T; Xu, G, 2021
)
2.06
"Cyclopropane is a sweet-smelling, irritating gas."( Sudden death by inhalation of cyclopropane.
Krause, JG; McCarthy, WB, 1989
)
1.29

Toxicity

ExcerptReferenceRelevance
" Our study not only showed that a safe chemical V6 could be turned to be toxic by NPs, but also pointed out a potential risk caused by the joint toxicity of 'safe' chemicals and plastic particles with small size."( Enhanced toxicity of 2,2-bis(chloromethyl) trimethylene bis[bis(2-chloroethyl) phosphate] (V6) by nanopolystyrene particles towards HeLa cells.
Hou, S; Li, J; Li, Z; Liu, X; Ruan, Y; Sun, L; Zhong, Z, 2023
)
0.91

Bioavailability

ExcerptReferenceRelevance
" A series of (1S,2R,3R)-2,3-dimethyl-2-phenyl-1-sulfamidocyclopropanecarboxylates was discovered to be potent, highly selective, and orally bioavailable aggrecanase inhibitors."( Discovery of (1S,2R,3R)-2,3-dimethyl-2-phenyl-1-sulfamidocyclopropanecarboxylates: novel and highly selective aggrecanase inhibitors.
Andrews, SW; Aoki, K; Fryer, AM; Haas, J; Hase, Y; Hotta, T; Imai, H; Inaba, T; Josey, JA; Kotoku, M; Laird, ER; Littmann, NM; Maeda, K; Matsuda, I; Mimura, T; Miura, T; Shinozaki, Y; Shiozaki, M; Suma, A; Tanaka, M; Ubukata, M; Yamasaki, T; Yasue, K; Yokota, M; Yoshiuchi, H, 2011
)
0.86

Dosage Studied

ExcerptRelevanceReference
" Maximum tolerated doses (MTD) for all five compounds in a NCr-nu mouse model were determined at dosing schedules of q1d x 5 (ip) in two cycles with a break of 10 days between cycles."( Cyclopropane-containing polyamine analogues are efficient growth inhibitors of a human prostate tumor xenograft in nude mice.
Basu, HS; Bhattacharya, S; Blokhin, AV; Brummel, S; Church, D; Frydman, B; Kink, JA; Marton, LJ; Maxuitenko, Y; Reddy, VK; Sarkar, A; Valasinas, A; Wilding, G, 2003
)
1.76
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
inhalation anaestheticnull
[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 (2)

ClassDescription
cycloalkaneSaturated monocyclic hydrocarbons (with or without side chains).
cyclopropanesCyclopropane and its derivatives formed by substitution.
[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]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID603952In-vitro blood to lung partition coefficients of the compound, logP(lung) (human/rat)2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID603950In-vitro air to lung partition coefficients of the compound, logK(lung) (human/rat)2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID603951In-vitro air to blood partition coefficients of the compound, logK(blood) (human/rat)2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (803)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990378 (47.07)18.7374
1990's25 (3.11)18.2507
2000's146 (18.18)29.6817
2010's212 (26.40)24.3611
2020's42 (5.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 67.90

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 Index67.90 (24.57)
Research Supply Index6.82 (2.92)
Research Growth Index5.05 (4.65)
Search Engine Demand Index117.90 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (67.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.11%)5.53%
Reviews25 (2.74%)6.00%
Case Studies4 (0.44%)4.05%
Observational0 (0.00%)0.25%
Other881 (96.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Barbed Suture Versus Non-Barbed Suture for Posterior Colporrhaphy: A Randomized Controlled Trial [NCT04658784]72 participants (Actual)Interventional2020-08-14Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT04658784 (9) [back to overview]Number of Patients With Early Anatomic Recurrence
NCT04658784 (9) [back to overview]Suture Burden
NCT04658784 (9) [back to overview]American College of Surgeons National Surgical Quality Improvement Program (ACS NSQIP) 30-day Postoperative Complications.
NCT04658784 (9) [back to overview]Change in Bowel Function Scores
NCT04658784 (9) [back to overview]Change in Pelvic Organ Prolapse Symptoms
NCT04658784 (9) [back to overview]Change in Postoperative Sexual Function Scores
NCT04658784 (9) [back to overview]Number of Patients With Subjective Failure
NCT04658784 (9) [back to overview]Operative Time
NCT04658784 (9) [back to overview]Surgery Specific Adverse Events (AEs) Measured at 6-months.

Number of Patients With Early Anatomic Recurrence

To evaluate anatomical failure of posterior compartment using a standard definition of anatomical cure will be defined as Ba or Bp at NCT04658784)
Timeframe: Week 6

InterventionParticipants (Count of Participants)
Intervention0
Control0

[back to top]

Suture Burden

To evaluate amount of suture burden present at time of surgery in posterior by compartment by measuring total amount of delayed absorbable suture used for posterior colporrhaphy in centimeters. (NCT04658784)
Timeframe: At time of surgery (Intraoperative)

Interventioncentimeters (Median)
Intervention10.5
Control26.9

[back to top]

American College of Surgeons National Surgical Quality Improvement Program (ACS NSQIP) 30-day Postoperative Complications.

To evaluate differences in adverse outcomes, using number of adverse events (AEs) as defined by the American College of Surgeons National Surgical Quality Improvement Program (ACS NSQIP) 30-day postoperative complications criteria. These criteria were reviewed at the week 6 data collection time interval. (NCT04658784)
Timeframe: 30 days

,
InterventionAdverse events (Number)
Urinary tract infection (UTI)Surgical site infection (SSI)ReadmissionReturn to the operating room (OR)Unplanned reintubation
Control31001
Intervention50110

[back to top]

Change in Bowel Function Scores

To evaluate change in bowel function using the Pelvic Floor Distress Inventory- 20 (PFDI-20) sub-scale Colorectal-Anal Distress Inventory-8 (CRADI-8). Total score (range 0 to 100) with the higher the score the more distress. (NCT04658784)
Timeframe: Baseline, Week 6, and month 6

,
Interventionscore on a scale (Mean)
baseline6 weeksChange from baseline to 6 weeks6 monthsChange from baseline to 6 months
Control36.618.1-18.69.6-27.9
Intervention36.418.1-18.212.3-24.1

[back to top]

Change in Pelvic Organ Prolapse Symptoms

To evaluate change in pelvic organ prolapse symptoms using the Pelvic Floor Distress Inventory- 20 (PFDI-20) sub-scale the Pelvic Organ Prolapse Distress Inventory- 6 (POPDI-6). Total score (range 0 to 100) with the higher the score the more distress. (NCT04658784)
Timeframe: Baseline, Week 6, and Month 6

,
Interventionscore on a scale (Mean)
baseline6 weekschange from baseline to 6 weeks6 monthsChange from baseline to 6 months
Control52.111.2-40.98.3-43.1
Intervention53.413.8-39.67.2-46.7

[back to top]

Change in Postoperative Sexual Function Scores

To evaluate postoperative sexual function using the Pelvic Organ Prolapse-Urinary Incontinence Sexual Function Questionnaire (PISQ-12). Total score (range 0 to 48) with a lower score associated with poorer/worse sexual function. (NCT04658784)
Timeframe: Month 6

,
Interventionscore on a scale (Mean)
Baseline6 monthsChange from baseline to 6 months
Control26.931.74.6
Intervention28.133.13.9

[back to top]

Number of Patients With Subjective Failure

"To evaluate subjective failure of posterior compartment using a negative response on POPDI-6 portion of the PFDI-20 questionnaire to questions: Do you usually have a sensation of bulging or protrusion from the vaginal area? and Do you usually have a bulge or something falling out that you can see or feel in the vaginal area?" (NCT04658784)
Timeframe: Week 6 and Month 6

,
InterventionParticipants (Count of Participants)
6 weeks6 months
Control02
Intervention01

[back to top]

Operative Time

To evaluate operative time for posterior repair in minutes. (NCT04658784)
Timeframe: Time of Surgery

,
InterventionMinutes (Median)
Total procedure surgical timePosterior repair surgical time
Control16820.5
Intervention14621

[back to top]

Surgery Specific Adverse Events (AEs) Measured at 6-months.

To evaluate differences in adverse outcomes, using number of surgery specific adverse events. (NCT04658784)
Timeframe: month 6

,
InterventionAdverse events (Number)
de novo dyspareunianew or worsening pelvic pain >3monthsNew or worsening constipation > 3 monthsNew fecal incontinenceNerve injuryOtherClassified as Severe Adverse Event (SAE)
Control5411001
Intervention4121111

[back to top]