chemistry

Tazarotene

Tazarotene is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Tazarotene rather than just read about it. In short: Tazarotene, sold under the brand name Tazorac, among others, is a third-generation prescription topical retinoid. It is primarily used for the treatment of plaque psoriasis and acne.

Key takeaways

Tazarotene belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Tazarotene to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Tazarotene from memory before moving on to harder problems.

Reference excerpt

Tazarotene, sold under the brand name Tazorac, among others, is a third-generation prescription topical retinoid. It is primarily used for the treatment of plaque psoriasis and acne. Tazarotene is also used as a therapeutic for photoaged and photodamaged skin. It is a member of the acetylenic class of retinoids. Tazarotene was approved for medical use in 1997 and is available as a generic medication.

Medical uses Tazarotene is most commonly used topically to treat acne vulgaris, psoriasis, and photoaging. Like other topical retinoids, such as tretinoin and adapalene, tazarotene can be used in a regimen with benzoyl peroxide and/or an oral antibiotic, such as clindamycin or dapsone, for the treatment of acne. This results in increased efficacy compared to tazarotene monotherapy. Combination therapy utilizing tazarotene alongside a mid- to high-potency corticosteroid is more effective in treating psoriasis compared to monotherapy of either drug. Tazarotene can also be used for the treatment of photodamaged skin. It can reduce the histological and clinical signs of photodamaged skin, such as fine lines, wrinkles, hyperpigmentation, and lentigo. The therapy is more effective when used with the daily application of sunscreen.

Available forms Tazarotene is available in several topical formulations, including gels, creams, foams, and lotions, with concentrations ranging from 0.045% to 0.1%. Tazarotene was first approved in 1997 as a 0.05% and 0.1% gel, followed by 0.05% and 0.1% creams in 2000. In 2012, a 0.1% aerosol foam was introduced to provide easier application to hair-bearing or large surface areas of the skin. A 0.045% lotion was approved in 2019, which utilizes a polymeric emulsion technology to stabilize the active ingredient at a lower concentration with increased absorption. Tazarotene is also available as a fixed-dose combination drug in the topical formulation of halobetasol/tazarotene for use in psoriasis.

Contraindications Tazarotene is contraindicated for use in patients who are known to be or suspected of being pregnant. Tazarotene is a known teratogen.

Pregnancy Before 2015, tazarotene was considered a Category X drug (meaning its use was contraindicated during pregnancy) according to US Food and Drug Administration (FDA) guidelines, despite demonstrating similar plasma retinoid levels as adapalene and tretinoin, which were classified as Category C drugs. Under the FDA's updated Pregnancy and Lactation Labeling Rule which eliminated the lettered pregnancy categories and came into effect in 2015, tazarotene was determined to be contraindicated in pregnancy. Because of the lack of pregnancy outcomes data for the drug, the determination was based on the teratogenic effects observed in rat and rabbit studies.

Adverse effects Adverse effects for tazarotene include skin irritation, such as redness, itchiness, and burning. In patients with psoriasis, these adverse effects can be mitigated by a combined treatment with either mometasone furoate or fluocinonide. These effects tend to be mild to moderate, and increase in intensity as tazarotene concentration increases.

Pharmacology

Mechanism of action Tazarotene is selective for two types of retinoic acid receptors, RAR-γ and RAR-β. Like all retinoids, it affects the ability of keratinocytes in the epidermis to proliferate and differentiate. It does so by upregulating filaggrin expression and downregulating the expression of keratinocyte transglutaminase, ornithine decarboxylase, involucrin, epidermal growth factor receptor, and various keratins.

Pharmacokinetics More than 99% of tazarotenic acid, the active metabolite of tazarotene, in the blood binds to plasma proteins (the most predominant being albumin). The volume of distribution (VD) for tazarotene is 26.1 L/kg and the VD for tazarotenic acid is 1.97 L/kg. Tazarotene is excreted from the body via feces and urine equally, and it has an elimination half-life of 16 to 18 hours.

Synthesis Acetylenic retinoid prodrug converted to the active metabolite, tazarotenic acid, with selective affinity for retinoic acid receptors RARβ and RARγ.

The formation of the ring system involves first alkylation of the anion from thiophenol with dimethylallyl bromide (1) to give the thioether (2). Friedel-Crafts cyclization of the olefin with the equivalent of PPA then gives the thiopyran (3). Acylation with acetyl chloride in the presence of aluminium chloride gives the methyl ketone (4). Reaction of the enolate of that ketone with diethyl chlorophosphate gives the enol phosphate 5 as a transient intermediate. This eliminates diethyl phosphite in the presence of excess base to give the corresponding acetylene 6. The anion from the reaction of the acetylene with base is then used to displace chlorine from Ethyl 6-chloronicotinate (7). This reaction affords the coupling product tazarotene (8).

Research

Melanoma

It is believed that Tazarotene may inhibit melanoma growth through the tazarotene-induced genes (TIG) family (TIG1, TIG2, TIG3) by specifically suppressing the mTOR pathway, inducing endoplasmic reticulum stress, and promoting cell differentiation and apoptosis. It further modulates the tumor microenvironment by enhancing immune surveillance (primarily through TIG2-mediated recruitment of natural killer and T cells) and may reduce pro-tumorigenic inflammatory markers like IL-6. These mechanisms collectively suppress myeloid-derived suppressor cells (MDSC), tumor proliferation, invasion, and metastasis, positioning tazarotene-regulated pathways as potential targets for melanoma immunotherapy.

References

Illustrations

Worked examples

Example 1 — a first encounter with Tazarotene

Start with the simplest possible case. Write down what Tazarotene claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Tazarotene before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Tazarotene ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Tazarotene

In research: Tazarotene appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Tazarotene in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Tazarotene is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alkyne derivatives, Anti-acne preparations, Antipsoriatics, so understanding it makes those chapters shorter.
In everyday life: Look for Tazarotene outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Tazarotene in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Tazarotene means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Tazarotene out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Tazarotene in simple terms?

Tazarotene, sold under the brand name Tazorac, among others, is a third-generation prescription topical retinoid. It is primarily used for the treatment of plaque psoriasis and acne.

Why does Tazarotene matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Tazarotene?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Tazarotene.