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PT III - DEENT > Dermatology MedChem (Sikazwe) > Flashcards

Dermatology MedChem (Sikazwe) Flashcards

1
Q

Terms:

UVR
PUVA
Mab
TNF
IgG1
A 
Ultra Violet Radiation
Psoralen + UVA
Monoclonal antibody
Tumor Necrosis Factor
Recombinant human immunoglobulin
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2
Q

VIS wavelength of ___-___ nm

A

400-700

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3
Q

UVA:

- wavelength of ___ (or ___) to ___

A

UltraViolet A

- 315 (or 320) to 400

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4
Q

UVB:

- wavelength of ___ to ___ (or ___)

A

UltraViolet B

- 280 to 315 (or 320)

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5
Q

Topical agents (9)

A
  • Emollients
  • Tars
  • Anthralin
  • Psoralen (Topical/Oral)
  • Corticosteroids
  • Vitamin D3 Analogs
  • Retinoids (Topical/Oral)
  • Macrolide
  • Immunosuppressants
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6
Q

Systemic agents (2 major)

A
  • Biologicals

- Non-Biologicals

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7
Q

Non-Biological Systemic agents (3)

A
  • Methotrexate
  • Cyclosporine
  • Mycophenolate
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8
Q

TOPICALS - Emollients

________ - mostly H2O emulsions (prevent skin H2O loss)

  • ________ (most effective, ___ Carbons)
  • Lanolin (odorus, wool grease)
  • Silicone based (hypoallergenic & non-comedogenic)
    • _________: straight chain structure
    • _________: a pentameric cyclic structure
A

Emollients

  • Petrolatum, >25
  • Silicone based:
    • Dimethicone
    • Cyclomethicone
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9
Q

TOPICALS - Tars

MOA unknown, but may have ____-_________ activity

____ Tar (e.g. Neutrogena T-Gel ®)

  • Mixture of phenols, PAHs & heterocyclic compounds
  • May be used with ___
  • Photosensitizer

Non-photosensitizers (2):

  1. ________ Tar
  2. ________ Tar
A

anti-proliferative

Coal Tar
- UVB

  1. Shale Tars (Ichthammol)
  2. Wood Tars
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10
Q

TOPICALS - Anthralin or Dithranol (e.g. Psoriatec):

  • Have ____-_________ properties
  • A _____________ derivative of anthracene
  • ________ paste (anthralin + ZnO + parrafin + salicylic acid)

MOA: Generates free ________ (oxygen super anion)

A
  • anti-proliferative
  • hydroxyanthrone
  • Lassar’s

radicals

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11
Q

Topicals: Psoralens

  • classified as _____________
    8-Methoxypsoralen (Methoxsalen, 8-MOP)
    *5-Methoxypsoralen (Bergapten, 5-MOP)
    *4,5’,8-trimethylpsoralen (Trioxsalen, TMP)
A

furanocoumarins

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12
Q

Topicals: Psoralens

  • Psoralen + UVA light (315-400nm) = PUVA:
    MOA:
    ________ binding to __________ in DNA,
    ↓ of DNA synthesis (antiproliferative)
A

Covalent… pyrimidines

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13
Q

Topicals: Psoralens
ADMET (8-MOP)

  • Potently Inhibits ___ ___ (key for Caffeine, Nicotine metabolism)
  • “_________ based inhibition” or “_______ inhibition”
A
  • CYP 2A6

- Mechanism, or suicide

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14
Q

Topicals: Glucocorticoids

  • produced in…
A
  • adrenal cortex
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15
Q

Topicals: Glucocorticoids

SAR:
\_\_ keto ↑ glucocorticoid activity
\_\_\_ β-keto ↑ activity
\_\_-\_\_ db ↑ activity
\_\_-\_\_ db ↑ activity
\_\_\_ _-substituent ↑ activity

__ and/or __ __________, ↑ both lipophilicity & potency, prevent oxidation of Ketone

A
  • C3 keto
  • C17 β-keto
  • C1-C2 db
  • C4-C5 db
  • C11 O-
  • C6 and/or C9 halogenation
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16
Q

Topicals: Glucocorticoids

Potency rankings for topical glucocorticoids:
Based on (3):
  • Super-potent (e.g., _________ _________ _.__% cream & ointment)
  • Potent (e.g., _________ ___________ _.__% cream & ointment)
  • Medium potency (e.g., ________ ________ .% cream)
  • Low potency (e.g.,_________ ______ .% & _% creams & ointments)
A

Based on:

1) chemical structure;
2) delivery vehicle;
3) % conc. in formulation

  • Clobesterol proprionate 0.05%
  • Betamethasone dipropionate 0.05%
  • Betamethasone valerate 0.1%
  • Hydrocortisone acetate 0.5% & 1%
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17
Q

Topicals: Vitamin D Analogs….
Calcitriol (Rocaltrol ®)
Calcipotriene (Dovonex ®)

Uses (2)

A

1) bone health;

2) Antiproliferatives

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18
Q

Topicals/Orals: Retinoids

  • Normalize ___________ & ____________
Topical agent(s):
\_\_\_\_\_\_\_\_\_ - Acetylenic retinoid

Oral Agents (2)

A
  • keratinization & proliferation

Tazarotene (Tazorac ®)

Acitretin (Soriatane ®)
Isotretinoin (Accutane ®)

19
Q

Topicals: Immunosuppressants

__________ ________ - ↓ release of inflammatory __________ from mast cells

  • Pimecrolimus (Elidel ®) - ______ skin protein binding
  • Tacrolimus (FK-506, Protopic ®)

Note: Both are ____ penetrating into skin

A

Calcineurin inhibitors
cytokines

  • higher;

less

20
Q

Systemic agents: Non-Biologicals
Methotrexate or MTX (Folex, Mexate):

  • Antiproliferative - Inhibits __________ _________ (DHFR) - ________ DNA/RNA synthesis
  • Immuno-suppressant & Anti-inflammatory effects
A
  • Dihydrofolate Reductase

inhibits

21
Q

Systemic agents: Non-Biologicals
Methotrexate or MTX (Folex, Mexate):

SAR

  • ______ ring, p-Amino Benzoic Acid, Glutamic Acid
  • Aromaticity of the _______ ring should be maintained for ________
  • Aromatic _-alkylation ↓ activity
  • _-___ is essential for activity
A
  • Pteridine,
  • pteridine, activity
  • N-
  • N-CH3
22
Q

Systemic agents: Non-Biologicals
Methotrexate or MTX (Folex, Mexate):

ADMET

Absorption: PO variable due to __________

Distribution: 50-70% bound; DDIs - displaced by ______ drugs (sulfonamides, salicylates, etc.)

Metabolism: 7-OH-MTX

Elimination: 80 % (______)

Toxicity: e.g. acute renal toxicity ….. _________ precipitation in urine (hydration/ urine alkalinization can help)

A 
A: ionization
D: acidic
M: 7-OH-MTX
E: urine
T: 7-OH-MTX
23
Q

Systemic agents: Non-Biologicals
Cyclosporine:

  • A “______” Immunosuppressant
  • Activated by complexation with _________ receptor
  • Inhibits _________ ________ & T-cell production
  • 11 Amino Acid cyclic peptide
A
  • prodrug
  • ciclophilin
  • calcineurin phosphatase
24
Q

Systemic agents: Non-Biologicals
Mycophenolate:

  • A “_______” Immunosuppressant
  • Rapidly forms ___ after PO or IV

MPA = ___________ _____:

  • Potent, selective, non-competitive & reversible inhibitor of _____
  • Inhibits _- & _-___________ proliferation
  • Inactivated by phenolic Glucuronidation to ____
A
  • prodrug
  • MPA

= Mycophenolic Acid

  • IMPDH
  • T- & B-lymphocytes
  • MPAG
25
Q

Acne Overview:

4 major components:

Treatment Goals (4)

A

components:

  • Increased sebum production
  • Excessive follicular keratinization
  • Bacterial (P. acnes) growth
  • Inflammation

treatment goals:

  • Normalize follicular keratinization
  • Decrease sebaceous gland activity
  • Decrease P. acnes colonization
  • Decrease inflammation
26
Q

Acne Treatment Agents (4)

A
  • Keratolytics
  • Retinoids
  • Hormones
  • Antibiotics
27
Q

Acne:

Keratolytics (4)

A
  • Glycolic Acid (AHA)
  • Salicylic Acid
  • Sulfur
  • Benzoyl peroxide
28
Q

Acne: Keratolytics

SAR:

  • ____ group(s)
  • __ group on the carbon _____ to –COOH group
A
  • COOH

- OH, alpha

29
Q

Acne: Keratolytics

Glycolic Acid

  • An ____-hydroxy acid
  • Hydrophylic Acid
  • Higher concs.- for deeper skin peels
  • Metabolized to ______ ____
A
  • alpha-

- to oxalic acid

30
Q

Acne: Keratolytics

Salicylic Acid

  • Promotes __________ (shedding)
  • More _________ than glycolic acid
  • May be irritating, but is generally well tolerated
A
  • desquamation

- lipophylic

31
Q

Acne: Keratolytics

Sulfur (monotherapy or mixtures)
S + Sulfacetamide (Plexion ®, Avar ®)
S + Zinc Oxide

MOA
– Unclear, but …..Sulfur reacts with _______ on skin cells to produce ___ which degrades keratin

A
  • cysteine, H2S
32
Q

Acne: Keratolytics

Benzoyl peroxide:

(e. g. Oxy-10 ®, Clearsil ®, ProActive ®)
- Has _________ effects - Propionibacterium Acnes
- Is absorbed in the skin & forms ________ ____
- Benzoic acid – rapidly excreted in ______

A
  • antibiotic
  • benzoic acid
  • urine
33
Q

Acne: Retinoids

\_\_\_\_\_\_\_\_\_
- Derivatives of Vitamin \_\_ (retinol)
- Act via retinoid receptors: \_\_\_ (alpha, beta, gamma) and \_\_\_
1- Anti-\_\_\_\_\_\_\_\_\_ properties
2- Anti-\_\_\_\_\_\_\_\_\_ properties
3- ↓ \_\_\_\_\_ production
A

Retinoids

  • A1
  • RAR and RXR

1- inflammatory
2- proliferative
3- sebum

34
Q 
Acne: Retinoids Biosynthesis
Beta-Carotene
    to
Retinal   \_\_\_\_\_\_  
  to
ATRA    \_\_\_\_\_\_\_\_\_

SAR:

  • The acid form is active at retinoid _______ (-____ group is essential)
  • 1st & 2nd gen. retinoids are _______
  • 3rd gen. retinoids are _______
A

Retinol

Isotretinoin

SAR:

  • receptors, (-COOH)
  • polyenes
  • polyaryls
35
Q

Acne: Retinoids 1st generation

_________ (Vitamin A1) - parent compound

___-_____ retinoic acid - 1st retinoid for acne

__-___ retinoic acid - Geometric isomer of Tretinoin

A

Retinol

All-Trans

13-cis

36
Q

Acne: Retinoids 2nd generation

  • Etretinate (Tegison ®):
  • _____ _____ Prodrug
  • T1/2 (___ ____) - highly lipophilic
  • Removed from U.S. market in 1998 due to teratogenicity
  • ______ Therapeutic Index
  • *Acitretin (Soriatane ®):
  • ______ form of Etretinate
A

*

  • Ethyl Ester
  • 120 days
  • Narrow
  • *
  • Active
37
Q

Acne: Retinoids 3rd generation

*Adapalene (Differin ®)
1st ________ retinoid
Lipophilic

Tazarotene (Tazorac ®)
Tazarotenic Acid (active metabolite)
A

synthetic

38
Q

Acne: Retinoids 3rd generation
ADMET:

Tazarotene
Low systemic \_\_\_\_\_\_\_\_\_ – low sytemic \_\_\_\_ \_\_\_\_\_\_
- rapidly metabolized
- short t1/2
- Do not accumulate in \_\_\_\_\_ \_\_\_\_\_\_\_
- Equally excreted in \_\_\_\_\_ and \_\_\_\_\_
A

absorption
side effects

  • fatty tissue
  • urine and feces
39
Q

Acne: Hormones (OCs)

OCs work on _________ triggers of acne:

Hormonal adjunct therapy in females (2)

A

hormonal

  1. Ethinyl Estradiol & Norgestimate (Ortho Tri-Cyclen Lo®)
  2. Ethinyl Estradiol & Drospirenone (Yasmin®, Yaz®)
40
Q

Hormones: Antiandrogens

Steroidal AA: _____________

Non-Steroidal AA:
1.
2.

Both estrogenic/anti-androgenic agents regulate _________ ______ and prevent _______ _______ production

A

Spironolactone (Aldactone)

  1. Flutamide (Eulexin)
  2. Ketaconazole

androgen levels
excess sebum

41
Q

Wrinkles (Fine/coarse) & pigmentary changes in the skin due to (3)

A

1) UVR
2) Smoking
3) Xenobiotic insult

42
Q

Sunscreens (UVA/UVB)
Physical Sunscreens -

Topical preparations include (2)

Notes:

  • Are broad spectrum (UVA & UVB)
  • _____ - do not irritate the skin
  • Available in ________ formulations
A
  • Reflect, scatter & absorb UVR on skin
  1. Zinc Oxide (ZnO)
  2. Titanium Dioxide (TiO2)
  • inert
  • micronized
43
Q 
Chemical sunscreens: (organic) compounds that absorb UVR
UVA (315-400 nm) Absorber(s):
Dibenzoylmethanes
Avobenzone
Absorbs the full spectrum  of  UVA
Rapidly degraded by UVA
A

-

PT III - DEENT (12 decks)

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